Name: 117-34-0|2,2-Diphenylacetic acid|98%
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SKU: A106893
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1
[ 67-56-1 ]
[ 117-34-0 ]
[ 1016-09-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With pyridine; copper(II) bis(trifluoromethanesulfonate); acetonitrile In toluene at 20℃; Irradiation; Inert atmosphere;	General procedure for etherification General procedure: To an oven-dried Schlenk tube (diameter of 1.5 cm), carboxylic acid (0.3 mmol), alcohol (0.3-1.5 mmol, 1-5 equiv.) and Cu(OTf)2 (0.75 mmol, 271.3 mg) were added, followed by toluene (2.85 ml), freshly distilled pyridine (0.9 mmol, 73 μl) and acetonitrile (0.15 ml). The reaction mixture was degassed by a freeze-pump-thaw cycle for four 4-min cycles and refilled with nitrogen. It was then irradiated for variable periods of time in front of a 40-W blue LED lamp. The reaction mixture was diluted with ethyl acetate or diethyl ether (2 ml) and then washed with deionized water (2 × 5 ml). The aqueous layer was extracted with ethyl acetate or diethyl ether (5 ml). The combined organic layers were dried over Na2SO4 and concentrated and purified by flash column chromatography.
	With pyridine; potassium hydroxide Electrolysis;

Reference： [1]Li, Qi Yukki; Gockel, Samuel N.; Lutovsky, Grace A.; DeGlopper, Kimberly S.; Baldwin, Neil J.; Bundesmann, Mark W.; Tucker, Joseph W.; Bagley, Scott W.; Yoon, Tehshik P. [Nature Chemistry, 2022, vol. 14, # 1, p. 94 - 99]
[2]v. d. Hoek; Nauta [Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 845,847]

2
[ 67-56-1 ]
[ 117-34-0 ]
[ 3469-00-9 ]

Yield	Reaction Conditions	Operation in experiment
98.7%		(1) Preparation of methyl 2,2-diphenylacetate To a 500 mL three-opening flask were added 2,2-diphenylacetic acid (20 g, 94 mmol) and 200 mL dichloromethane. After stirring, 1 mL DMF was added. To the mixture was slowly added oxalyl chloride (13.16 g, 104 mmol) dropwisely in an ice bath. The reaction was conducted at 25 C. After the completion of reaction, the mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (100 mL) and anhydrous methanol (3.61 g, 113 mmol) dropwisely under cooling in an ice bath respectively. The reaction was conducted at 25 C. After the completion of reaction, the reaction solution was washed with a saturated aqueous NaCl solution. The organic phase was dried over sodium sulfate, and filtered by suction. The filtrate was evaporated to dryness to produce methyl 2,2-diphenylacetate (21 g) in a yield of 98.7%.
98.7%	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 25℃;Cooling with ice;	(1) Preparation of methyl 2,2-diphenylacetate To a 500mL three-opening flask were added 2,2-diphenylacetic acid (20g, 94mmol) and 200mL dichloromethane. After stirring, 1mL DMF was added. To the mixture was slowly added oxalyl chloride (13.16g, 104mmol) dropwisely in an ice bath. The reaction was conducted at 25C. After the completion of reaction, the mixture was evaporated under reduced pressure to remove oxalyl chloride. To the reaction flask were slowly added dichloromethane (100mL) and anhydrous methanol (3.61g, 113mmol) dropwisely under cooling in an ice bath respectively. The reaction was conducted at 25C. After the completion of reaction, the reaction solution was washed with a saturated aqueous NaCl solution. The organic phase was dried over sodium sulfate, and filtered by suction. The filtrate was evaporated to dryness to produce methyl 2,2-diphenylacetate (21 g) in a yield of 98.7 %.
93%	With sulfuric acid;Reflux;	Methyl 2,2-diphenylacetate To a stirred solution of 2,2-diphenylacetic acid (1 gram, 1 equiv) in dry MeOH (50 mL) was added sulfuric acid (0.4 mL) dropwise and heated to reflux. Stirring was then continued for 3 hours. The reaction mixture was then cooled and poured into saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic fractions were dried over Na2SO4, filtered, and concentrated under reduced pressure to yield an oil (1.0 g, 93%) that was not further purified.

84.37%

With sulfuric acid; at 80℃; for 2h;

A mixture of compound (AA) (280.00 g, 1.32 mol, 1.00 eq.) was dissolved in MeOH (1.4 L), and then H2SO4 (140.00 mL) was added. The mixture was stirred at 80 C. for 2 h and monitored by TLC (PE:EA=5:1), which showed no starting material after 2 h. The mixture was concentrated. The residue was washed with aq. NaHCO3 (2000 mL) and extracted with EA (1000 mL). The organic layer was concentrated to give compound (BB) (280 g, 84.37%). 1H NMR: (CDCl3, 400 MHz): delta7.38-7.29 (m, 10H), 5.07 (s, 1H), 3.78 (s, 3H).

Reference： [1]Patent: US2014/45896,2014,A1 .Location in patent: Paragraph 0159; 0160
[2]Patent: EP2703398,2014,A1 .Location in patent: Paragraph 0143; 0144
[3]Patent: US2010/35872,2010,A1 .Location in patent: Page/Page column 11
[4]Tetrahedron,2007,vol. 63,p. 12720 - 12730
[5]Patent: US2017/260189,2017,A1 .Location in patent: Paragraph 0060; 0061
[6]Chinese Journal of Chemistry,2020,vol. 38,p. 565 - 569
[7]Journal of the American Chemical Society,1988,vol. 110,p. 871 - 876
[8]Bulletin of the Chemical Society of Japan,1958,vol. 31,p. 860
[9]Chemische Berichte,1895,vol. 28,p. 2786
[10]Collection of Czechoslovak Chemical Communications,1960,vol. 25,p. 736 - 742
[11]Journal fur praktische Chemie (Leipzig 1954),1990,vol. 332,p. 755 - 761
[12]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 2283 - 2297
[13]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 503 - 517
[14]Journal of Organic Chemistry,2019,vol. 84,p. 1468 - 1488
[15]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4783 - 4788

3
[ 117-34-0 ]
[ 603-54-3 ]
[ 4695-14-1 ]

Reference： [1]Chemische Berichte,1953,vol. 86,p. 945

4
[ 117-34-0 ]
[ 1871-76-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With thionyl chloride	4.1 (1) (1) Diphenylacetic acid chloride 21.2 g (0.1 mol) of diphenylacetic acid and 75 ml (about 1 mol) of thionyl chloride are mixed cold. The reaction mixture is heated under reflux for 3 hours and is cooled, the excess thionyl chloride is evaporated and the acid chloride (crystallized at a low temperature, melting point < 50° C.) is collected. 22.9 g of acid chloride (yield about 99%) are thus obtained.
96%	With thionyl chloride In benzene for 2h; Reflux;
90%	With thionyl chloride for 1h; Heating;

86%	With thionyl chloride for 2h; Heating;
85%	With thionyl chloride In toluene for 7.5h; Heating / reflux;	A The preparation of diphenylketene. The preparation of diphenylketene was carried out according to the published procedure starting from diphenylacetic acid. [Taylor, E. C. , et al. , Org Synth CV 6,549.] A. Diphenylacetyl chloride.; A 500 mL, three-necked flask equipped with a dropping funnel and a reflux condenser carrying a calcium chloride drying tube was charged with diphenylacetic acid (50.0 g, 0.236 mol) and anhydrous toluene (150 mL). The mixture was heated under reflux, and thionyl chloride (132 g, 80.1 mL, 1.11 mol) was added dropwise over 30 minutes. Refluxing was continued for 7 additional hours and then the toluene and excess thionyl chloride were removed by distillation under reduced pressure. The residue was dissolved in 150 mL of refluxing, anhydrous hexane. The hot solution was treated with charcoal and filtered, and the filtrate was cooled to 0°C in a sealed flask. The product, which crystallizes as colorless plates was filtered, washed with a little cold hexane, dried at 25°C under vacuum giving diphenylacetyl chloride (46 g, 85%), m. p. 51-52°C.
68%	With Amberlite IRA 93 (PCl₅ form) In dichloromethane for 6h; Heating;
	With thionyl chloride
	With phosphorus(V) chloride
	With phosphorus(V) chloride; trichlorophosphate
	With thionyl chloride
	With oxalyl dichloride In benzene for 3h; Ambient temperature;
	With thionyl chloride In dichloromethane for 12h; Heating; Yield given;
	With oxalyl dichloride In 1,4-dioxane for 3h; Heating;
	With thionyl chloride for 15h;
	With thionyl chloride at 90 - 100℃; for 3h;
	With thionyl chloride for 1h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In benzene for 2h; Ambient temperature;
	With thionyl chloride In toluene for 4h; Heating;
	With thionyl chloride for 2h; Heating;
	With thionyl chloride for 2h; Heating;
	With oxalyl dichloride In dichloromethane at 0 - 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In benzene for 18h;
	With oxalyl dichloride
	With thionyl chloride In benzene Heating;
	With thionyl chloride for 0.75h; Heating;
	With thionyl chloride for 0.25h; Heating;
	With thionyl chloride In benzene for 4h; Heating;
	With thionyl chloride In dichloromethane for 1.5h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 12h;
	With thionyl chloride In dichloromethane for 1.5h; Heating;
100 % Spectr.	With trichloroacetonitrile; triphenylphosphine In chloroform-d1 at 20℃; for 0.25h;
	With thionyl chloride for 2h; Heating;
	With thionyl chloride; N,N-dimethyl-formamide
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
	With thionyl chloride for 2h; Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃;
	With thionyl chloride In chloroform
	With thionyl chloride at 20 - 50℃; for 1.5h;
	With trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃; Inert atmosphere;
	With thionyl chloride at 0℃; Reflux;
	With thionyl chloride for 3h; Reflux;	General procedure: Compound 10 was prepared by a procedure similar to that of Lu and co-workers, and Nagao and co-workers. A solution of octanoic acid (4.43g, 30.74mmol) and thionyl chloride (20mL) was heated under reflux for 3h. The excess thionyl chloride was removed in vacuo and the crude octanoyl chloride taken through to the next step without further purification. A solution of 2 (12.0g, 21.55mmol), triethylamine (4.6mL, 33.3mmol), dimethylaminopyridine (0.26g, 2.16mmol) and crude octanoyl chloride in dimethylformamide (150mL) was then stirred at room temperature for 3h. The mixture was then diluted with ethyl acetate (200mL) and washed with water (200mL). The separated aqueous phase was further extracted with ethyl acetate (2×100mL) and the combined organic phases washed with brine (4×100mL), dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. Purification by flash chromatography (hexane/ethyl acetate 2:1) afforded 10 as an off-white solid (9.92g, 14.66mmol, 68%).
	With thionyl chloride at 80℃; for 6h;
	With oxalyl dichloride; N,N-dimethyl-formamide In chloroform at 20℃; for 1h; Inert atmosphere;
	With thionyl chloride; N,N-dimethyl-formamide In toluene at 0℃; for 3h; Reflux;
	With thionyl chloride Reflux;
	With thionyl chloride Reflux;
	With thionyl chloride Reflux;	5.1.1. N-(3-Bromopropyl)-3,5-dichlorobenzamide (10a) Compound 9a (191 mg, 1 mmol) was refluxed in excess of thionylchloride (3 mL) overnight. Excess of thionyl chloride was evaporatedand the residue was dissolved in CH2Cl2, 3-bromopropylamine hydrobromide (328 mg, 1.5 mmol was addedfollowed by triethylamine (TEA; 0.42 mL, 3 mmol). The reactionmixture was stirred at room temperature. After the reaction wascompleted, the reaction mixture was diluted with CH2Cl2 andsequentially washed with water, 1 N HCl and saturated NaHCO3.The organic layer was dried over MgSO4, filtered and concentrated.The obtained product was purified by column chromatographywith n-hexane/ethyl acetate (EtOAc) = 4:1 to obtain 10a, (236 mg,76%) as white solid.
	With I,I-bischloroiodobenzene; triphenylphosphine In dichloromethane for 0.166667h; Reflux; Inert atmosphere;
	With thionyl chloride at 50 - 60℃;
	With phosphorus trichloride at 50 - 60℃;	In a 250 ml reaction flask, I (20.0 g) was added, stirred, phosphorus trichloride (100 ml) was added, heated to 50-60 ° C, the gas was absrobed from the lye, and reacted for 3-4 h. After completion of the reaction, the organic layer was separated to obtain brown liquid 2,2-diphenylacetyl chloride (formula II).
	Multi-step reaction with 2 steps 1: magnesium(II) sulfate; sulfuric acid / dichloromethane / 20 °C / Inert atmosphere 2: thionyl chloride; lithium hydroxide monohydrate / 20 °C / Sealed tube
	With thionyl chloride In tetrahydrofuran; toluene; benzene Reflux;	4.1.27. N-(2-Chloroethyl)-2,2-diphenylacetamide (18a) Compound 17a (530 mg, 2.49 mmol) was refluxed in excess of thionyl chloride (10 mL) in presence of benzene for overnight. Excess of thionyl chloride and benzene was evaporated and the residue was dissolved in CH2Cl2, 2-chloroethylamine hydrochloride(432 mg, 3.73 mmol) was added followed by triethylamine(TEA; 1 mL, 7.47 mmol). The reaction mixture was stirred at room temperature. After the reaction was completed, the reaction mixture was diluted with CH2Cl2 and sequentially washed with water,1 N HCl and saturated NaHCO3. The organic layer was dried overMgSO4, filtered and concentrated. The obtained product was purified by column chromatography with n-hexane: Ethyl acetate(EtOAc) = 4:1 to obtain 18a (386 mg, 60%) as light yellow liquid.Rf = 0.82 (n-hexane: EtOAc = 1:1). 1H NMR (300 MHz, CDCl3): d7.43-7.33 (m, 11H), 3.73-3.65 (m, 4H).
	In dichloromethane at 20 - 80℃; for 1h;
	With thionyl chloride In benzine for 24h; Inert atmosphere; Reflux;	5.8. General procedure for the synthesis of diphenylacetic acid chloride (18) A solution of diphenylacetic acid 17 (5 g, 23.56 mmol) in benzene (10 mL) was treated by the dropwise addition of SOCl2 (42 g, 0.35 mol, 26 mL) under nitrogen atmosphere. Then the reaction mixture was heated at reflux with stirring for 24 h, cooled to room temperature and stirred for another 24 h. Next, the excess of SOCl2 and benzene were removed under vacuum to obtained desired acid chloride 18 as a colorless oil, which solidified on standing. Diphenylacetic acid chloride (18) was further used without any purification.
	Stage #1: 2,2-diphenylacetic acid With oxalyl dichloride In dichloromethane for 0.333333h; Inert atmosphere; Stage #2: With N,N-dimethyl-formamide In dichloromethane for 2h; Inert atmosphere;
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 55℃; for 5h;
	With thionyl chloride In dichloromethane for 6h; Reflux;
	With tungsten hexachloride In dichloromethane-d2 for 18h; Inert atmosphere;
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;
	With thionyl chloride at 90℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h;
	With chlorinating agent In dichloromethane at 0℃;
	With thionyl chloride at 25℃; for 0.5h; Inert atmosphere;
	With thionyl chloride In toluene at 55℃; for 0.5h;
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 4h; Inert atmosphere;
	With thionyl chloride In benzene for 12h; Reflux;	Synthesis of 1,2-13C-labeled diphenylacetyl chloride (8) General procedure: According to the literatures,6,7 a solution of 1,2-13C-labeled diphenylacetic acid (7) (7.15 g, 33.4 mmol) and thionyl chloride (5.0 mL, 70 mmol) in dry benzene (5.0 mL) was refluxed for 12 h, and then residual thionyl chloride was removed by distillation under reduced pressures. 1,2-13C-Labeled diphenylacetyl chloride (8) (6.71 g, 28.8 mmol) was obtained as a colorless solid by distillation using a glass tube oven and recrystallization in hexane. 8 was immediately used for the next stage.
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1h;	9.8; 10.1 [0145] 2,2-diphenylacetic acid (37 mg, 0.17 mmol) and DMF (1 drop) were added to dry dichloromethane (10 mL). After cooling to 0 °C, oxalyl chloride (27 mg, 0.21 mmol) was added, stirred at room temperature for 1 hour, and then concentrated under reduced pressure. The residue was dissolved in dichloromethane (2 mL) to obtain a 2,2-diphenylacetyl chloride solution. C283-8 (40 mg, 0.14 mmol) and triethylamine (28 mg, 0.28 mmol) were dissolved in dichloromethane (5 mL) and cooled to 0 °C. The previous 2,2-diphenylacetyl chloride solution was then slowly added. The reaction solution was allowed to react at room temperature for 5 hours. LC-MS indicated that the reaction of the starting materials was complete. Dichloromethane (30 mL) was added, washed with saturated brine (20 mL 3), dried over anhydrous sodium sulfate for 30 min and then filtered. The filtrate was concentrated under reduced pressure to obtain a crude compound. The crude product was subjected to separation by thin layer chromatography (petroleum ether:ethyl acetate=2:1) to obtain Compound C283-9 (30 mg, a colorless oily liquid, yield: 44%). MS m/z (ESI): 470.0 [M+H] +.
	With thionyl chloride at 100℃;
	With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 85℃; Inert atmosphere; Schlenk technique;

Reference： [1]Current Patent Assignee: LAFON L LAB; LABORATOIRE L LAFON MAISONS ALFORT VAL DE MARNE FR; RABO ERU RAFUON; LAFON LABOR - US4122186, 1978, A
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[51]Greenberg, Jacob A.; Sammakia, Tarek [Journal of Organic Chemistry, 2017, vol. 82, # 6, p. 3245 - 3251]
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5
[ 117-34-0 ]
[ 4695-13-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; di-<i>tert</i>-butyl dicarbonate; ammonium bicarbonate In 1,4-dioxane at 20℃; for 12h;	1.1 10 g (47.1 mmol) of diphenyl acetic acid and 12.34 g (56.5 mmol, 1.2 eq) of (Boc)2O were added. 2.2 g (28.3 mmol, 0.6 eq) of pyridine and 5.6 g (70.7 mmol, 1.5 eq) Of NH4HCO3 were added thereto. Then, 100 ml of 1,4-dioxane was added thereto to dissolve them. Thereafter, the solution was stirred for 12 hours at room temperature. After the reaction was completed, the reactant was extracted with an organic layer by using EA/H2O. The organic layer was concentrated, and then diethyl ether was added for crystallization thereto. The resultant solution was stirred for 1 hr and then filtered to obtain 9.49 g (95%) of 2,2-diphenyl-acetamide. 1H NMR (200 MHz, CDCl3) δ 7.35-7.27 (m, 10H) 5.99 (brs, IH) 5.60 (brs, IH)
92%	With magnesium(II) nitrate hexahydrate; urea In octane at 120℃; for 24h;
86%	Stage #1: 2,2-diphenylacetic acid With thionyl chloride In tetrahydrofuran at 50℃; for 1h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0℃; for 0.0833333h;

77%	Stage #1: 2,2-diphenylacetic acid With thionyl chloride In N,N-dimethyl-formamide at 85℃; for 1.5h; Stage #2: With ammonium hydroxide In tetrahydrofuran at -5 - 0℃;	2,2-diphenylacetamide (S5) The mixture of 15 g 2,2-diphenylacetic acid, 10 ml thionyl chloride and DMF (3 drops) was heated at85 C for 1.5 h. The excess thionyl chloride was removed under reduced pressure and the residue wasdissolved in dry THF. The resulting solution was carefully added to aqueous NH3 at -5-0 C. Amide (S7)was filtered and washed with water. S5 was obtained in 77% yield (11.5 g).S7: 1H NMR (400.1 MHz, CDCl3) δH: 7.51-7.28 (m, 10H, 2*Ph), 6.03 (br s, 1H from NH), 5.60 (br s, 1Hfrom NH2), 4.98 (s, 1H, CH).
	With diethyl ether; ammonia at 230℃; im geschlossenen Rohr;
	Multi-step reaction with 2 steps 1: thionyl chloride 2: ammonia
	Multi-step reaction with 2 steps 1: PCl₅ 2: NH₃
		3.a a. a. 2,2-Diphenylacetamide The title compound was prepared using the method of Example 2a substituting an equivalent quantity of diphenylacetic acid for (3,4-dimethoxyphenyl)acetic acid as the starting acid. The title compound was isolated as a white solid, mp 168°-171° C.
	Multi-step reaction with 2 steps 1: thionyl chloride / 0.5 h / 25 °C / Inert atmosphere 2: ammonia / water / 0.5 h / 25 °C
	Multi-step reaction with 2 steps 1: thionyl chloride / toluene / 0.5 h / 55 °C / 750.08 Torr 2: ammonia / methanol / 0.5 h / 55 °C

Reference： [1]Current Patent Assignee: CGK - WO2007/15632, 2007, A1 Location in patent: Page/Page column 31
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6
[ 117-34-0 ]
[ 1883-32-5 ]

Yield	Reaction Conditions	Operation in experiment
92%		In the inert gas N2 atmosphere, after dehydration and deoxidation treatment to the reaction bottle after adding diphenyl acetic acid (105.8 mg, 0.5 mmol, gun for adding [...] borane (289 mul, 2 mmol), reacting at room temperature 12 hours, the reaction out of the glove box, in order to have three methoxybenzene (83.84 mg, 0.5 mmol) as the internal standard, CDCl3 for dissolving, stirring 10 minutes, sampling, with nuclear magnetic resonance. Calculated 1 H and the yield is 99%. The product of nuclear magnetic data: The residue is added to the sample in 1 g silica gel, in order to 3 ml methanol as a solvent, 50 C lower reaction 3 h, the borate further hydrolysis alcohol, after the reaction, extracted with ethyl acetate three times, the combined organic layer, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the silica gel (100 - 200 mesh) column chromatography purification, ethyl acetate/hexane (1:5) mixture as the eluent, to obtain the pure primary alcohol, separation and the yield is 92%.
86%	With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate); In toluene; at 80℃; for 16h;sealed tube;	General procedure: In a sealed tube, 29 mg Cu(OTf)2 (0.08 mmol, 8 mol %) and 0.7 mL TMDS (537 mg, 4 mmol, 8 Si-H mol/mol substrate) were introduced to a solution of aliphatic carboxylic acid (1 mmol) in 1.5 mL toluene. After stirring 16 h at 80 C, the reaction mixture was cooled to room temperature and quenched with 4 mL H2O. The organic layer was extracted with CH2Cl2, dried with anhydrous MgSO4, and evaporated under reduced pressure. The crude was purified by silica gel column chromatography to obtain the alcohol.

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[21]Patent: CN109467498,2019,A

7
[ 80-65-9 ]
[ 117-34-0 ]
[ 70298-81-6 ]

Reference： [1]Pharmazie,1979,vol. 34,p. 12 - 13

8
[ 117-34-0 ]
[ 37517-78-5 ]
[ 25022-02-0 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2943 - 2949

9
[ 117-34-0 ]
[ 119-61-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With trimethylamine-N-oxide; copper chloride (I) In acetonitrile at 60℃; for 24h; other diaryl acetic acid, copper(I) or copper(II) chloride;
97%	With 1H-imidazole; sodium (meta)periodate; 5,10,15,20-tetrakis-(4-aminophenyl) manganese(III) porphyrin chloride In water monomer; acetonitrile at 25℃; for 0.833333h;	General procedure for oxidative decarboxylation of carboxylic acid with NaIO₄ catalyzed by [Mn(TNH₂PP)Cl(at)MWCNT] General procedure: In a 25 mL flask equipped with a magnetic stirring bar, a solution of NaIO4 (2 mmol in 10 mL H2O) was added to a mixture of α-aryl carboxylic acid (1 mmol), [Mn(TNH2PP)Cl(at)MWCNT] (300 mg, 0.043 mmol) and imidazole (0.2 mmol) in CH3CN (10 mL). The progress of the reaction was monitored by TLC. After the reaction was completed, the catalyst was filtered and washed with EtOH. At the end of the reaction, the reaction mixture was diluted with Et2O (20 mL) and filtered. The catalyst was thoroughly washed with Et2O and combined washings and filtrates were purified on silica-gel plates or with a silica-gel column. The identities of the products were confirmed by IR and 1H NMR spectral data.
96%	With oxygen; tetra-N-butylammonium tribromide In ethyl acetate at 20℃; for 23h; Irradiation;

95%	With mercury(II) fluoride; oxygen In acetonitrile at 25℃; for 24h; Irradiation;
95%	With 1H-imidazole; sodium (meta)periodate In water monomer; acetonitrile at 20℃; for 45h;
95%	With 1H-imidazole; C₁₇H₁₆ClMnN₂O₂; tetrabutylammonium (meta)periodate In chloroform at 20℃; for 0.5h;
95%	With K₅CoW₁₂O₄₀ In water monomer; acetonitrile for 0.133333h; Microwave irradiation;
94%	With sodium (meta)periodate; dibenzo-18-crown-6; benzyl-triethyl-ammonium chloride In ethanol for 4h; Heating;
92%	With potassium peroxodisulfate In water monomer at 90℃; for 12h; Green chemistry;	General Procedure for the preparation of Aldehydes and Ketones from Aryl acetic acids General procedure: In an oven dried tube containing a mixture of 4-methyl phenyl acetic acid 1a (200 mg, 1.33mmol) and potassium persulfate (360 mg, 2.66 mmol), water (2 mL) was added and heated at 90 °C for 12 h. Upon completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature (24°C) and it was extracted with ethyl acetate (3 x 5 mL). The crude product was purified by column chromatography to furnish compound 2a as colorless liquid (136 mg, 85% yield).
92%	With oxygen; Mn(dtbpy)<SUB>2</SUB>(OTf)<SUB>2</SUB> In acetonitrile at 45℃; for 12h; Irradiation; Schlenk technique;
91%	With copper(II) ferrite In dimethyl sulfoxide at 120℃; for 10h; Green chemistry;
90%	With dinitratocerium (IV) chromate In benzene for 0.5h; Heating;
90%	With Caswell No_. 744A; [bis(acetoxy)iodo]benzene In acetonitrile at 0 - 20℃; for 0.25h;
86%	With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; anhydrous sodium carbonate; ethyl viologen diperchlorate In dimethyl sulfoxide at 20℃; for 16h; Irradiation;
85%	With tetrabutylammonium (meta)periodate In 1,4-dioxane for 48h; Heating;
85%	With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.5h; Heating;
84%	With [bis(acetoxy)iodo]benzene; bromine In various solvent(s) for 22h; Heating; irradiation;
82%	With Cu(NO₃)2*3 H₂O on montmorillonite K₁₀ clay; dihydrogen peroxide for 0.025h; under microwave irradiation;
81%	With ferric(III) chloride; oxygen In N,N-dimethyl-formamide at 110℃;
78%	With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; 1,1,3,3-tetramethylguanidine In acetonitrile at 20℃; for 6h; Irradiation;	2.1 Experimental procedure for synthesis of 2a-2q General procedure: To a 25 mL reaction tube, arylacetic acid (0.2 mmol), 4CzIPN (1 mol%), TMG (50 mol%) were dissolved in CH3CN (1.5 mL), and then the tube was stirred in air at room temperature for 6 h with the irradiation of 25 W blue LEDs. After reaction, the mixture was collected, and the residue was purified by column chromatography on silica gel to afford the desired products.
78%	With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC]iridium hexafluorophosphate; anhydrous sodium carbonate In dimethyl sulfoxide Irradiation; Flow reactor;
77%	With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;
70%	With Ag-Ag₂S nanoparticles supported on cellulose In water monomer at 80℃; for 0.05h; Microwave irradiation; Green chemistry;
57%	With oxygen; copper atom In acetonitrile at 50℃; for 15h;
57%	With air; copper atom In acetonitrile at 50℃; for 15h; various carboxylic oxids decarboxylated;
57%	With potassium peroxodisulfate; water monomer; anthranilic acid amide at 80℃; Sealed tube;
55%	With CuO₂H In acetonitrile at 75℃; for 20h; under 30W sonication;
53%	With tris(2,2′-bipyridine)ruthenium(II) dichloride hexahydrate; 1-butoxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In 2,2,2-trifluoroethanol at 40℃; for 3h; UV-irradiation;
	With 1H-imidazole; tetraphenylporphinatomanganese(III) cyanide; tetrabutylammonium (meta)periodate In dichloromethane at 20℃;
11 %Spectr.	With FSM-16; air In hexane at 20℃; for 30h; Irradiation;
> 99 %Chromat.	With 2',3',4',5'-tetra-O-acetylriboflavin; water monomer In acetonitrile for 0.333333h; Irradiation;
	With 5,10,15,20-tetraphenyl-21H,23H-porphine manganese(III) chloride; oxygen In hexane at 150℃; for 4h;
80 %Chromat.	With 2',3',4',5'-tetra-O-acetylriboflavin; hydrogenchloride; scandium trifluoromethanesulphonate In water monomer; acetonitrile for 2.5h; UV-irradiation;
	Stage #1: 2,2-diphenylacetic acid for 0.05h; Inert atmosphere; Stage #2: With tert.-butylhydroperoxide at 75℃; for 72h; Inert atmosphere;
	With 1H-imidazole; [bis(acetoxy)iodo]benzene; Co(AAOPD) In acetonitrile at 20℃;
	Multi-step reaction with 2 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Schlenk technique; Inert atmosphere 1.2: Schlenk technique; Inert atmosphere; Cooling 1.3: 20 °C / Schlenk technique; Inert atmosphere; Cooling 2.1: 1,10-Phenanthroline; tris(2,4-pentanedionato)iron(III) / 1,2-dichloro-ethane / 12 h / 80 °C / Inert atmosphere; Sealed tube

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[35]Soleymani, Reza; Taheri, Milad; HOSEYNALIBEYGl, Marziye; Daryani, Mehdi [Oriental Journal of Chemistry, 2012, vol. 28, # 2, p. 857 - 866,10]
[36]Li, Wen-Cheng; Liao, Wei-Wei; Sun, Yun-Hai; Wei, Zhong-Lin; Wu, Yu-Heng; Xi, Ji-Ming [Organic Letters, 2022, vol. 24, # 4, p. 1110 - 1115]

10
[ 117-34-0 ]
[ 106-95-6 ]
[ 6966-03-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 2,2-diphenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 0 - 45℃; Stage #2: allyl bromide In tetrahydrofuran at 20 - 45℃;
80%	Stage #1: 2,2-diphenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 0 - 60℃; Stage #2: allyl bromide In tetrahydrofuran at 0 - 25℃; Stage #3: With water; ammonium chloride In tetrahydrofuran
71%	Stage #1: 2,2-diphenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 25 - 60℃; for 1.5h; Stage #2: allyl bromide In tetrahydrofuran at 60℃; for 2h;

	With lithium diisopropyl amide 1.) THF, hexane, 23 deg C, 1 h, 2.) 23 deg C, 16 h; Yield given. Multistep reaction;
	With lithium diisopropyl amide 1.) THF, 0 deg C, then 25 deg C, 1 h and 60 deg C, 0.5 h, 2.) 0 deg C, then 25 deg C, 16 h; Multistep reaction;
	Stage #1: 2,2-diphenylacetic acid With n-butyllithium In tetrahydrofuran at 0℃; Stage #2: allyl bromide In tetrahydrofuran at 0℃;
296 g (99%)	With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane	VIII 2,2-DIPHENYL-4-PENTENOIC ACID EXAMPLE VIII 2,2-DIPHENYL-4-PENTENOIC ACID A solution of diphenylacetic acid (250 g., 1.17 mol) in 2.4 L of tetrahydrofuran was stirred at 0° C. under argon while 0.94 L of a 2.5M solution on n-butyllithium in hexane was added dropwise. After 1 hour, allyl bromide (142.5 g, 1.17 mole) was added in one portion. After 15 minutes, 500 mL of 10% hydrochloric acid was added, along with ether (2 L). The layers were separated, the aqueous layer extracted with ethyl ether (1*250 mL), the organic layers combined, washed with brine, dried (MgSO4), and filtered. Concentration afforded 296 g (99%) of an off-white solid, mp 134°-137° C. 1H NMR (CDCl3)δ 7.3 (m, 10H), 5.6 (m, 1H), 4.9 (bs, 2H), 3.2 (d, 2H).
	Stage #1: 2,2-diphenylacetic acid With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	Preparation of 2,2-diphenylpent-4-enoic acid This reaction was performed in oven-dried glassware under a nitrogen atmosphere. To a well-stirred solution 2.5M -BuLi (8.27 ml, 20.68 mmol, 2.20 equiv) in hexanes, the starting acid (2.0 g, 9.4mmol, 1.0 equiv) was dissolved in dry 100 ml tetrahydrofuran and added dropwise during 0.5 hours at -78 °C. The mixture was allowed to stir for 1 hour then ally bromide (1.52 g, 12.69 mmol, 1.35 equiv) was added dropwise over 0.5 h at the same temperature. The reaction mixture was stirred overnight at room temperature, quenched with 10% HQ (while cooling in ice bath) until acidic (pH :::: 2). The organic layer was separated and the aqueous layer was extracted with ether (3 x 50mL). The organic phases were combined and washed with brine. The solution was then dried over MgS04 and concentrated in vacuo to afford a crude oil which was purified through flash chromatography (silica; ethyl acetate/hexanes, 10% ~ 20%) to provide 2,2-dipheiiylpent-4-enoic acid: 1H NMR (400 MHz, CDC13) δ 7.37 - 7.17 (m, I ON ). 5.58 (ddt, J - 19.1 , 9.6, 6.9 Hz, 1 H), 4.98 - 4.85 (rn. 2H), 3.16 (d, J = 7.0 Hz, 2H).
	Stage #1: 2,2-diphenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 0 - 45℃; for 0.5h; Stage #2: allyl bromide In tetrahydrofuran at 45℃; for 4h;
	Stage #1: 2,2-diphenylacetic acid With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: allyl bromide at -78℃; for 0.5h;	Preparation of 2,2-diphenylpent-4-enoic acid: This reaction was performed in oven- dried glassware under a nitrogen atmosphere. To a well-stirred solution of 2.5M n-BuLi (8.27 ml, 20.68 mmol, 2.20 equiv) in hexanes, the starting acid (2.0 g, 9.4mmol, 1.0 equiv) was dissolved in dry 100 ml tetrahydrofuran and added dropwise during 0.5 hours at -78 °C. The mixture was allowed to stir for 1 hour, and then allyl bromide (1.52 g, 12.69 mmol, 1.35 equiv) was added dropwise over 0.5 h at the same temperature. The reaction mixture was stirred overnight at room temperature, quenched with 10% HC1 (while cooling in ice bath) until acidic (pH = 2). The organic layer was separated and the aqueous layer was extracted with ether (3 x 50 mL). The organic phases were combined and washed with brine. The solution was then dried over MgSO4 and concentrated in vacuo to afford a cmde oil which was purified through flash chromatography (silica; ethyl acetate/hexanes, 10% 20%) to provide 2,2-diphenylpent- 4-enoic acid. ‘H NMR (400 MI-Tz, CDC13) ö 7.37-7.17 (m, 1OH), 5.58 (ddt, J = 19.1, 9.6, 6.9 Hz, 1H), 4.98-4.85 (m, 2H), 3.16 (d, J = 7.0 Hz, 2H).
	Stage #1: 2,2-diphenylacetic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 45℃; for 1.5h; Stage #2: allyl bromide In tetrahydrofuran; hexane at 45℃;	Alkenoic Acids 9a-h; General Procedure¹⁸ General procedure: To a solution of i-Pr2NH (2.5 equiv) in THF (4.0 M) at 0 °C was slowly added n-BuLi (1.63 M in hexane, 2.5 equiv), and the mixture was stirred at 0 °C for 1 h. To the solution was added the appropriate α,α-disubstituted acetic acid (1.0 equiv) in THF (0.8 M), and the mixture was stirred at 45 °C for 1.5 h. Allyl bromide (2.0 equiv) was added to the solution and the mixture was stirred at 45 °C overnight. H2O was added to the mixture and the aqueous layer was washed with Et2O. The aqueous layer was acidified with aq HCl, and the mixture was extracted with Et2O (3 x). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated on a rotary evaporator. The solid residue was recrystallized from CHCl3 and hexane to give 9.
	Stage #1: 2,2-diphenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 0 - 55℃; Stage #2: allyl bromide In tetrahydrofuran at 0 - 55℃;
	Stage #1: 2,2-diphenylacetic acid With lithium diisopropyl amide In tetrahydrofuran at 0 - 40℃; for 2h; Stage #2: allyl bromide In tetrahydrofuran at 0 - 40℃; for 2.5h;

Reference： [1]Barczak, Nicholas T.; Jarvo, Elizabeth R. [Chemistry - A European Journal, 2011, vol. 17, # 46, p. 12912 - 12916]
[2]Cottrell, Ian F.; Cowley, Andrew R.; Croft, Laura J.; Hymns, Lauren; Moloney, Mark G.; Nettleton, Ewan J.; Kirsty Smithies; Thompson, Amber L. [Tetrahedron, 2009, vol. 65, # 12, p. 2537 - 2550]
[3]Kang, Yan-Biao; Chen, Xian-Min; Yao, Chuan-Zhi; Ning, Xiao-Shan [Chemical Communications, 2016, vol. 52, # 36, p. 6193 - 6196]
[4]Halterman, Ronald L.; McEvoy, Marjorie A. [Journal of the American Chemical Society, 1990, vol. 112, # 18, p. 6690 - 6695]
[5]Miller, R. D.; Goelitz, P. [Journal of Organic Chemistry, 1981, vol. 46, # 8, p. 1616 - 1618]
[6]Tsutsui, Hideyuki; Yamaguchi, Yukiko; Kitagaki, Shinji; Nakamura, Seiichi; Anada, Masahiro; Hashimoto, Shunichi [Tetrahedron Asymmetry, 2003, vol. 14, # 7, p. 817 - 821]
[7]Current Patent Assignee: SANOFI - US5039691, 1991, A
[8]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - WO2014/164756, 2014, A1 Location in patent: Paragraph 0255
[9]Zhang, Zhi-Qiang; Liu, Feng [Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6690 - 6693]
[10]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION - WO2016/183150, 2016, A1 Location in patent: Paragraph 0292
[11]Nagamoto, Midori; Nishimura, Takahiro; Yorimitsu, Hideki [Synthesis, 2017, vol. 49, # 18, p. 4272 - 4282]
[12]Rao, Wei-Hao; Jiang, Li-Li; Liu, Xiao-Meng; Chen, Mei-Jun; Chen, Fang-Yuan; Jiang, Xin; Zhao, Jin-Xiao; Zou, Guo-Dong; Zhou, Yu-Qiang; Tang, Lin [Organic Letters, 2019, vol. 21, # 8, p. 2890 - 2893]
[13]Chen, Suqing; Liu, Zhenghui; Mu, Tiancheng; Ou, Hualin; Tan, Xingxing; Wang, Peng; Yan, Zhenzhong; Yu, Dongkun; Zhao, Xinhui [RSC Advances, 2020, vol. 10, # 13, p. 7698 - 7707]

11
[ 117-34-0 ]
[ 530-62-1 ]
[ 80928-23-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane at 0 - 20℃; for 1h;	24.1 Example24: Alternative Synthesis of Compound 65 1. Procedure for the preparation of Compound 65f To a stirred solution of diphenyl acetic acid (5.0 g, 23.5 mmol) in DCM (50 mL) at 0°C was added GDI (4.6 g, 28.3 mmol) in portions and the mixture was stirred at RT for 1 h, TLC (DCM:MeOH=20: l) showed the starting material was consumed. The mixture was washed with water (30 mL x 2) and brine (30 mL x 2), dried over Na2S04, filtered and concentrated in vacuo to give 65f (5.6 g, 90%) as a white solid. LC-MS (Agilent): Rt 3.70 min; m/z calculated for C7H,4N20 [M+H]+ 263.1, found [M+H]+ 263.1.
83%	In dichloromethane at 20℃; for 2h; Inert atmosphere;
	In tetrahydrofuran at 22℃; for 18h;

	In tetrahydrofuran for 2h; Heating;
	In N,N-dimethyl-formamide at 40 - 45℃; for 0.333333h;
	In dichloromethane Ambient temperature;
	In tetrahydrofuran at 0 - 23℃;
	at 20℃; for 1h; Inert atmosphere;
	In acetonitrile at 20℃; for 1h;
	at 20℃; for 0.0833333h; Milling;
	With 4-morpholinecarboxaldehyde In toluene

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2013/102242, 2013, A1 Location in patent: Page/Page column 106
[2]Pal, Mohan; Khanal, Mandar; Marko, Ryan; Thirumalairajan, Srinath; Bearne, Stephen L. [Chemical Communications, 2016, vol. 52, # 13, p. 2740 - 2743]
[3]Bhattacharya, A.; Williams, J.M.; Amato, J.S.; Dolling, U.-H.; Grabowski, E.J.J. [Synthetic Communications, 1990, vol. 20, # 17, p. 2683 - 2690]
[4]Pometan; Dumas; Fourtillan; et al. [European Journal of Medicinal Chemistry, 1981, vol. 16, # 5, p. 425 - 429]
[5]Roufos; Hays; Dooley; Schwarz; Campbell; Probert Jr. [Journal of Medicinal Chemistry, 1994, vol. 37, # 2, p. 268 - 274]
[6]Ulibarri, Gerardo; Choret, Nadege; Bigg, Dennis C. H. [Synthesis, 1996, # 11, p. 1286 - 1288]
[7]Chatterjee, Sankar; Iqbal, Mohamed; Kauer, James C.; Mallamo, John P.; Senadhi, Shobha; Mallya, Satish; Bozyczko-Coyne, Donna; Siman, Robert [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 13, p. 1619 - 1622]
[8]Ghorai, Prasanta; Kraus, Anja; Keller, Max; Götte, Carsten; Igel, Patrick; Schneider, Erich; Schnell, David; Bernhardt, Günther; Dove, Stefan; Zabel, Manfred; Elz, Sigurd; Seifert, Roland; Buschauer, Armin [Journal of Medicinal Chemistry, 2008, vol. 51, # 22, p. 7193 - 7204]
[9]Yoganathan, Sabesan; Miller, Scott J. [Organic Letters, 2013, vol. 15, # 3, p. 602 - 605]
[10]Mocci, Rita; De Luca, Lidia; Delogu, Francesco; Porcheddu, Andrea [Advanced Synthesis and Catalysis, 2016, vol. 358, # 19, p. 3135 - 3144]
[11]Bianchi, Barbara; Cai, Chunlong; Grand-Guillaume Perrenoud, Alexandre; Hardegger, Leo A.; Humair, Roger; Kaehny, Richard; Lanz, Stephan; Li, Cheng; Li, Jialiang; Mallet, Franck; Rampf, Florian; Shi, Lei; Spoendlin, Christoph; Staüble, Jeannine; Teng, Shangjun; Tian, Xiangguang; Wietfeld, Bernhard; Yang, Yao; Yu, Bo; Zepperitz, Christine; Zhang, Xuesong; Zhang, Yong [Organic Process Research and Development, 2020, vol. 24, # 9, p. 1743 - 1755]

12
[ 117-34-0 ]
[ 23735-39-9 ]
[ 144042-75-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4415 - 4424

13
[ 117-34-0 ]
[ 100-51-6 ]
[ 37537-23-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With S,S-bis<4,6-dimethyl-2-pyrimidinyl> dithiocarbonate In dichloromethane for 2.5h; Ambient temperature;
83%	With 2-butyl-1,3-diphenyl-1,3,2-diazaphospholidine; 1,1'-azodicarbonyl-dipiperidine In 1,2-dichloro-ethane at 40℃;
81%	With pyridine; N-Bromosuccinimide; triphenylphosphine In dichloromethane; pentane for 2h; Ambient temperature;

80%

Stage #1: 2,2-diphenylacetic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h; Cooling; Stage #2: benzyl alcohol With triethylamine In dichloromethane at 20℃; for 1.83333h;

Preparation of benzyl benzoate by using PPh3/NCBT General procedure: To a cold solution of PPh3 (0.327 g, 1.25 mmol) in CH2Cl2 (3 mL), freshly prepared NCBT (0.194 g,1.25 mmol) was added with continuous stirring. Benzoic acid (0.122 g, 1 mmol) was then added and stirring was continued for 15 min. Benzyl alcohol (0.270 g, 2.5 mmol) was added and the temperature was raised up to room temperature. The pale yellow solution was neutralized by triethylamine (0.175 mL). Stirring was continued for 40 min at room temperature. The progress of the reaction was followed by TLC. Upon completion of the reaction, the concentrated residue was passed through a short silica-gel column using n-hexane-ethyl acetate (8:1) as eluent. Benzyl benzoate was obtained with 95% yield after removing the solvent under reduced pressure.

Reference： [1]Kim, Sunggak; Kim, Sung Soo [Synthesis, 1986, # 12, p. 1017 - 1019]
[2]Huang, Hai; Kang, Jun Yong [Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6604 - 6614]
[3]Froeyen, Paul [Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 91, # 1-4, p. 145 - 152]
[4]Rouhi-Saadabad, Hamed; Akhlaghinia, Batool [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 2, p. 253 - 263]

14
[ 91-01-0 ]
[ 117-34-0 ]
[ 13144-31-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sulfonated nanohydroxyapatite functionalized with 2-aminoethyl dihydrogen phosphate In dichloromethane at 41℃; for 3.5h;	Typical procedure for the preparation of benzhydryl benzoate in the presence of HAPAEPH₂-SO₃H General procedure: HAPAEPH2-SO3H (0.08 g, 8 mol %) was added to a solution of benzoic acid (1 mmol, 0.12 g) in dry dichloromethane (2 mL) at 41 °C. Benzhydrol (2 mmol, 0.368 g) was dissolved in dichloromethane (2 mL) and added to the reaction mixture dropwise during 1 h. Progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was removed by filtration. The filtrate was washed with distilled water (3 9 4 mL), dried over Na2SO4, and concentrated in vacuo to give the crude product which was then purified by thin layer chromatography using EtOAc/n-hexane (2:8) to afford benzhydryl benzoate (0.264 g, 95 %).
81%	With toluene-4-sulfonic acid In benzene Heating;
79%	With dmap; O,O'-di(2-pyridyl) thiocarbonate In toluene Ambient temperature;

Reference： [1]Siavashi, Narges Yousefi; Akhlaghinia, Batool; Zarghani, Monireh [Research on Chemical Intermediates, 2016, vol. 42, # 6, p. 5789 - 5806]
[2]Paredes, Rodrigo; Agudelo, Fernando; Taborda, Gonzalo [Tetrahedron Letters, 1996, vol. 37, # 12, p. 1965 - 1966]
[3]Saitoh, Katsuyuki; Shiina, Isamu; Mukaiyama, Teruaki [Chemistry Letters, 1998, # 7, p. 679 - 680]

15
[ 85-02-9 ]
[ 117-34-0 ]
Diphenyl-acetic acid; compound with benzo[f]quinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 6322 - 6325

16
[ 781-35-1 ]
[ 117-34-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hypochlorite; lithium hypochlorite In ethanol at 77℃; for 2h;

Reference： [1]Madler; Klucik; Soell; Brown; Liu; Berlin; Benbrook; Birckbichler; Nelson [Organic Preparations and Procedures International, 1998, vol. 30, # 2, p. 230 - 234]

17
[ 104-53-0 ]
[ 117-34-0 ]
[ 849020-94-6 ]
4-Diphenylacetyl-3-phenethyl-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 8047 - 8050

18
[ 5554-37-0 ]
[ 7553-56-2 ]
[ 64-19-7 ]
red phosphorus [ No CAS ]
[ 117-34-0 ]
[ 4695-14-1 ]

Reference： [1]Zhurnal Obshchei Khimii,1955,vol. 25,p. 189,191; engl. Ausg. S. 173

19
[ 117-34-0 ]
[ 102410-65-1 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
(S)-((R)-2-Diphenylacetylamino-5-guanidino-pentanoylamino)-phenyl-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1597 - 1600

20
[ 117-34-0 ]
[ 111524-95-9 ]
Fmoc-D-Arg(Pmc)-OH [ No CAS ]
(R)-((R)-2-Diphenylacetylamino-5-guanidino-pentanoylamino)-phenyl-acetic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1597 - 1600

21
[ 3469-00-9 ]
[ 117-34-0 ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 5648 - 5653
[2]Green Chemistry,2020,vol. 22,p. 4165 - 4173
[3]Monatshefte fur Chemie,2004,vol. 135,p. 83 - 87
[4]Synthetic Communications,2000,vol. 30,p. 4167 - 4171
[5]Journal of Medicinal Chemistry,2020

22
[ 117-34-0 ]
[ 37073-15-7 ]
[ 182318-00-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 8210 - 8213

23
[ 117-34-0 ]
[ 6638-79-5 ]
[ 93008-38-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 2,2-diphenylacetic acid; N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 18℃; for 0.25h; Stage #2: With tributylphosphine; (2-pyridine-N-oxide)disulfide In dichloromethane
82%	Stage #1: 2,2-diphenylacetic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 1h; chemoselective reaction;	General procedure for the synthesis of Weinreb amides General procedure: A. To a mixture of benzoic acid (50 mg, 0.41 mmol, 1 equiv), PPh3 (160 mg, 0.61 mmol, 1.5 equiv) and NBS (108.5 mg, 0.61 mmol, 1.5 equiv), CH2Cl2 (2 ml) was added and the reaction was stirred at 0 °C for 15 min. The reaction was brought to room temperature and N,O-dimethylhydroxylamine hydrochloride (59.5 mg, 0.61 mmol, 1.5 equiv) and Et3N (45.5 mg, 63 µl, 0.45 mmol, 1.1 equiv) were added and reaction was stirred for 1 h at room temperature. The reaction mixture was quenched with aqueous sodium bicarbonate solution and diluted with CH2Cl2. The bicarbonate washings were again extracted with CH2Cl2 and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. Column chromatography was performed using EtOAc/Petroleum ether (1:5).
79%	Stage #1: 2,2-diphenylacetic acid With trichloroacetonitrile; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;

73%

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Banwell; Smith [Synthetic Communications, 2001, vol. 31, # 13, p. 2011 - 2019]
[2]Pilathottathil, Fathima; Vineet Kumar, Doppalapudi; Kaliyamoorthy, Alagiri [Synthetic Communications, 2020, vol. 50, # 11, p. 1622 - 1632]
[3]Location in patent: experimental part Kim, Joong-Gon; Jang, Doo Ok [Bulletin of the Korean Chemical Society, 2010, vol. 31, # 1, p. 171 - 173]
[4]Guven, Sinem; Kundu, Gourab; Rissanen, Kari; Schoenebeck, Franziska; Ward, Jas S.; Weßels, Andrea [Journal of the American Chemical Society, 2021, vol. 143, # 22, p. 8375 - 8380]

24
[ 117-34-0 ]
[ 26487-67-2 ]
2-(hexahydro-1H-azepin-1-yl)ethyl diphenylethanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3244 - 3253

25
[ 6066-82-6 ]
[ 117-34-0 ]
[ 226218-61-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;
93%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	9 4.2.9 Succinimidyl diphenylacetate (20) To a stirred solution of diphenylacetic acid (25.0 g, 118.0 mmol) in anhydrous THF (500 mL) was added DCC (25.5 g, 124 mmol) and N-hydroxysuccinimide (14.2 g, 124 mmol). The reaction mixture was stirred at room temperature overnight, the white precipitate (DCU) was removed by filtration and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (eluent: PE/EtOAc 70:30 to 30:70) yielded the product as a white solid (33.9 g, 93%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.76 (s, 4H), 5.36 (s, 1H), 7.13-7.58 (m, 10H). 13C NMR (75 MHz, CDCl3): δ (ppm) 25.6, 54.0, 127.9, 128.7, 128.9, 136.7, 168.2, 169.0. MS (EI, 70 eV): m/z (%) 309 (5) M+⩽, 167 (100) [(Ph)2-CH]+⩽. C18H15NO4 (309.32).
88%	With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 1h;

72%

With dicyclohexyl-carbodiimide In dichloromethane for 2h; Cooling with ice;

Reference： [1]Keller, Max; Pop, Nathalie; Hutzler, Christoph; Beck-Sickinger, Annette G.; Bernhardt, Günther; Buschauer, Armin [Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8168 - 8172]
[2]Keller, Max; Kaske, Melanie; Holzammer, Tobias; Bernhardt, Guenther; Buschauer, Armin [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6303 - 6322]
[3]Shelkov, Rimma; Nahmany, Moshe; Melman, Artem [Organic and Biomolecular Chemistry, 2004, vol. 2, # 3, p. 397 - 401]
[4]Buschmann, Jonas; Keller, Max; Seiler, Theresa; Wifling, David; Bernhardt, Günther [2020, vol. 11, # 2, p. 274 - 282]

26
[ 117-34-0 ]
[ 62-53-3 ]
[ 4695-14-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 15h;Inert atmosphere;	General procedure: A solution of diphenylacetic acid (212 mg, 1.0 mmol), N-methylaniline (128 mg, 1.2mmol), DCC (247 mg, 1.2 mmol), and DMAP (24 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 15 h. After aqueous extractive workup and column chromatographic purification process (hexanes/Et2O,5:1) 1a was obtained as a white solid, 226 mg (75%). Other 2,2,N-triarylacetamides were prepared similarly from corresponding N-arylaminesand 2,2-diarylacetic acids. Diphenylacetic acid, bis(4-chlorophenyl)acetic acid and 9-fluorenecarboxylic acid were purchased from commercial sources, and other diarylacetic acids were prepared by Friedel-Crafts reaction of arenes and corresponding mandelic acid derivatives according to the reported methods.3,4

Reference： [1]Tetrahedron,2009,vol. 65,p. 3893 - 3899
[2]Tetrahedron Letters,2016,vol. 57,p. 784 - 787
[3]Journal of the American Chemical Society,2016,vol. 138,p. 13314 - 13325
[4]Russian Journal of Organic Chemistry,2004,vol. 40,p. 1469 - 1472
[5]Tetrahedron Letters,2005,vol. 46,p. 3751 - 3754
[6]Organic and Biomolecular Chemistry,2012,vol. 10,p. 3906 - 3912

27
[ 117-34-0 ]
[ 71989-31-6 ]
[ 175291-56-2 ]
Phosphoric acid mono-[(1R,2S)-3-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-diphenylacetylamino-1-methyl-3-oxo-propyl] ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4815 - 4823

28
[ 586-95-8 ]
[ 117-34-0 ]
[ 10382-20-4 ]

Yield	Reaction Conditions	Operation in experiment
58.8%	With dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 24h;	3.4 g (16.4 mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was added to a solution of 3.84 g (16.4 mmol) of diphenylacetic acid and 1.67 g (14.8 mmol) of 4-pyridylcarbinol in 50 mL of dichloromethane. The reaction mixture was stirred at room temperature for about 24 h. The urea precipitate was filtered off, and the filtrate was washed with (2 25 mL) NaHCO3 and (2 25 mL) water. The organic layer were collected and dried over MgSO4, and the solvent was evaporated yielding required compound.

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5547 - 5554
[2]Dyes and Pigments,2015,vol. 112,p. 24 - 33
[3]Journal of the American Chemical Society,2005,vol. 127,p. 8000 - 8001

29
[ 117-34-0 ]
[ 86-29-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium azide; TEA; triethylphosphine In dichloromethane; dimethyl sulfoxide at 0℃; for 30h;
88%	With sodium azide; triethylamine; triphenylphosphine In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 0.833333h;
	Multi-step reaction with 2 steps 1: diethyl ether; NH₃ / 230 °C / im geschlossenen Rohr 2: PCl₅; POCl₃

	Multi-step reaction with 3 steps 1: thionyl chloride 2: ammonia 3: thionyl chloride / 90 - 105 °C
	Multi-step reaction with 2 steps 1.1: thionyl chloride / tetrahydrofuran / 1 h / 50 °C 1.2: 0.08 h / 0 °C 2.1: palladium diacetate; Selectfluor; acetonitrile / 18 h / 20 °C

Reference： [1]Kangani, Cyrous O.; Day, Billy W.; Kelley, David E. [Tetrahedron Letters, 2008, vol. 49, # 5, p. 914 - 918]
[2]Kangani, Cyrous O.; Day, Billy W.; Kelley, David E. [Tetrahedron Letters, 2007, vol. 48, # 34, p. 5933 - 5937]
[3]Neure [Justus Liebigs Annalen der Chemie, 1889, vol. 250, p. 143,147]
[4]Hellerman; Cohn; Hoen [Journal of the American Chemical Society, 1928, vol. 50, p. 1728]
[5]Al-Huniti, Mohammed H.; Rivera-Chávez, José; Colón, Katsuya L.; Stanley, Jarrod L.; Burdette, Joanna E.; Pearce, Cedric J.; Oberlies, Nicholas H.; Croatt, Mitchell P. [Organic Letters, 2018, vol. 20, # 19, p. 6046 - 6050]

30
[ 110-89-4 ]
[ 117-34-0 ]
[ 4107-00-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dmap; benzenesulfonic anhydride In dichloromethane at 20℃; for 1h;
91%	With dmap In dichloromethane at 20℃; for 1h;
91%	With dmap In chloroform at 25℃; for 1h;

72%	Stage #1: 2,2-diphenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: piperidine In tetrahydrofuran at 0 - 20℃; for 16h;	To a solution of carbonyldiimidazole (CDI) (0.35 g, 2.14 mmol) in dry, freshly distilled THF (10 mL) under an argon atmosphere, was added diphenylacetic acid (454 mg, 2.14 mmol). The reaction mixture was allowed to stir at room temperature for 1 hour after which time it was cooled to 0° C. and piperidine (0.2 mL, 1.98 mmol) in THF (5 mL) was added. The reaction mixture was left at room temperature for 16 hours with stirring. The reaction mixture was poured onto aqueous saturated sodium hydrogen carbonate (20 mL) and dichloromethane (25 mL) was added. The organic layer was separated and the aqueous phase washed with dichloromethane (2×25 mL). The combined organic extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure.The crude product was recrystallised from acetone and isolated as white crystals in 72% yield.1H NMR (CDCl3): δ 6 1.20 (m, 2H, CH2); 1.48 (m, 4H, CH2); 3.33 (m, 2H, CH2); 3.55 (m, 2H, CH2); 5.15 (s, 1H, C(O)CH); 7.16-7.24 (aromatic CH).13C NMR (CDCl3): δ 24.5 (piperidine CH2); 25.6 (piperidine CH2); 26.1 (piperidine CH2); 43.4 (piperidine CH2); 47.1 (piperidine CH2); 54.8 (C(O)CH); 126.9 (aromatic CH×2); 128.4 (quaternary aromatic C); 128.5 (aromatic CH×4); 129.0 (aromatic CH×4); 139.7 (quaternary aromatic C); 170.0 (quaternary CO).EIMS: m/z 279 (4%, M+); 226 (3%); 167 (27%); 112 (43%); 68 (100%).HREIMS: m/z M+ 279.1628 (calculated for C19H21NO 279.1623)Melting Point: 119.6-120° C.Infrared νmax (KBr): 1637 s, 1493 w, 1435 m, 1357 w, 1278 w, 1250 m, 1219 m, 1135 w, 1017 m, 757 m, 709 s, 622 m cm-1 Anal.: Calculated for C19H21NO: C, 81.68, H, 7.58; N, 5.01. Found C, 81.73, H, 7.31; N, 5.12.
	Stage #1: 2,2-diphenylacetic acid With oxalyl dichloride; N,N-dimethyl-formamide at 0 - 20℃; for 1h; Stage #2: piperidine at 0 - 20℃;	H H. MMR-64. To a round. bottom flask equipped with stir bar containing toluene; 5 equivalents of diphenylacetic acid was added followed by 5 equivalents of DMF. The solution was allowed to stir at 0°C until the temperature had equilibrated. Upon reaching 0°C, the oxalyl chloride was added slowly, and the solution was allowed to warm to room temperature. It was stirred at room temperature for about 1 hour, upon which it was placed back onto ice (0°C) and piperidine (1 equivalent) was slowly added. The reaction was allowed to warm to room temperature and was stirred until completion. The toluene was removed by rotary evaporation and the amide was isolated. To a round bottom flask equipped with stir bar and dry THF, 1 equivalent of LiAPH4 and 1/3 equivalents of AlCl3 (relative to LiAlH4) were added slowly. The resulting solution was allowed to stir for about 1 hour. The amide formed hereinabove (1 equivalent) was dissolved in a minimal amount of THF and added to the stirring solution via syringe very slowly.

Reference： [1]Funasaka, Setsuo; Kato, Koji; Mukaiyama, Teruaki [Chemistry Letters, 2007, vol. 36, # 12, p. 1456 - 1457]
[2]Funasaka, Setsuo; Kato, Koji; Mukaiyama, Teruaki [Chemistry Letters, 2008, vol. 37, # 5, p. 506 - 507]
[3]Thirupathi Reddy; Narsimha Reddy; Raghotham Reddy; Crooks, Peter A. [Chemistry Letters, 2008, vol. 37, # 5, p. 528 - 529]
[4]Current Patent Assignee: NATIONAL UNIVERSITY OF SINGAPORE; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; MARITIME AND PORT AUTHORITY OF SINGAPORE - US2011/92518, 2011, A1 Location in patent: Page/Page column 9-10
[5]Current Patent Assignee: UNIVERSITY OF VIRGINIA - EP1165508, 2004, B1 Location in patent: Page 14

31
[ 117-34-0 ]
[ 4695-14-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1893,vol. 275,p. 84

32
[ 52023-68-4 ]
[ 117-34-0 ]
N-(6-morpholin-4-yl-pyridin-3-yl)-2,2-diphenyl-acetamide [ No CAS ]

Reference： [1]Patent: US6407120,2002,B1 .Location in patent: Page column 34

33
[ 1709-59-7 ]
[ 117-34-0 ]
N-(4-Dimethylsulfamoyl-phenyl)-2,2-diphenyl-acetamide [ No CAS ]

Reference： [1]Patent: US6407120,2002,B1 .Location in patent: Page column 37

34
[ 769-42-6 ]
[ 117-34-0 ]
[ 82756-66-9 ]

Yield	Reaction Conditions	Operation in experiment
59%	With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	8 EXAMPLE 8; 5-diphenylacetyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione (Dtpd-OH) 9 A mixture of 1,3-dimethylbarbituric acid (5.00 g, 32.05 mmol), diphenylacetic acid (10.19 g, 48.03 mmol), 4-dimethylaminopyridine (1.95 g, 16.01 mmol) in dry CH2Cl2 (30 ml) was cooled to 0 C. and 1,3-dicyclohexylcarbodiimide (7:26 g, 35.22 mmol) added. The reaction mixture was stirred at room temperature overnight and filtered. The solid was washed with CH2Cl2 (150 ml) and the combined solution was washed with 2 N HCl solution (40 ml). The organic phase was dried over MgSO4 and evaporated. The residue was crystallized from EtOH giving 5-diphenylacetyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 9 (6.70 g, 59%). Rf 0.64 (hexane/EtOAc/AcOH 10:5:0.1); FAB MS C20H18N2O4 (350.36) m/z (%) 373 [M+Na]+ (8), 351 [M+H]+ (100), 338 (24), 333 (16). 1H NMR (CDCl3) d 18.28 (s, 1H, OH), 7.32-7.27 (m, 10H, 10 ArH), 7.02 (s, 1H, CHAr2), 3.36, 3.31 (2s, 6H, 2 NCH3).

Reference： [1]Current Patent Assignee: VAST BIOSCIENCE - US6765089, 2004, B1 Location in patent: Page column 18

35
[ 547-64-8 ]
[ 117-34-0 ]
[ 27871-49-4 ]
[ 17392-83-5 ]
[ 1208982-48-2 ]

Yield	Reaction Conditions	Operation in experiment
47%	With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h; Inert atmosphere; Resolution of racemate; optical yield given as %ee; enantioselective reaction;
1: 68 % ee 2: 47%	With 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h;	5 Test Example 5Production of Optically Active 2-Hydroxy Ester Using Various Types of Racemic 2-Hydroxy Ester (3) As shown in the above reaction scheme, to diethyl ether (0.2 M) containing 0.6 equivalents of pivalic acid anhydride and 0.5 equivalents of diphenylacetic acid were added 1.2 equivalents of diisopropyl ethylamine, 5% by mole of (+)-benzotetramisole (BTM), and a solution containing 1 equivalent of a racemic 2-hydroxy ester in diethyl ether at room temperature in this order, and this reaction mixture was stirred at room temperature for 12 hrs. Thereafter, the reaction was stopped with a saturated aqueous sodium bicarbonate solution. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether three to five times. After the organic layers were admixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to afford a corresponding diester and unreacted optically active 2-hydroxy ester. The results are shown in Table 5. TABLE 5 Yield [%] [a] cc [%] No.R5 R6 5a; 5b 5a; 5b s 29 Et n-Pr 47; 47 97; 89 217 30 Me Me 47; 23 97; 68 119 [a] Isolation yieldAs is seen from Table 5, prominently high enantiomeric excess ee and reaction velocity ratio s were exhibited also when a material other than the benzyl ester was used (Entries 29 and 30).The physical properties of the optically active hydroxy esters and the diesters in Table 5 are shown below.(Entry 29)Ethyl (S)-2-hydroxypentanoate1H NMR (CDCl3): δ4.19 (dq, J=14.0, 7.0 Hz, 1H, Eta), 4.18 (dq, J=14.0, 7.5 Hz, 1H, Eta), 2.96 (br d, J=3.5 Hz, 1H, OH), 1.75-1.65 (m, 1H, 3-H), 1.62-1.52 (m, 1H, 3-H), 1.48-1.30 (m, 2H, 4-H), 1.24 (dd, J=7.5, 7.0 Hz, 3H, Eta), 0.89 (t, J=7.3 Hz, 3H, 5-H);13C NMR (CDCl3): δ175.3, 70.2, 61.4, 36.4, 17.9, 14.1, 13.6.Ethyl (R)-2-(diphenylacetyloxy)pentanoateHPLC (CHIRALCEL AD-H, i-PrOH/hexane=1/50, flow rate=1.0 mL/min): tR=15.0 min (1.4%), tR=17.5 min (98.6%);IR (neat): 1745, 1496, 1454, 745, 701 cm-1;1H NMR (CDCl3): δ7.33-7.17 (m, 10H, Ph), 5.08 (s, 1H, 2'-H), 4.98 (dd, J=7.0, 6.0 Hz, 1H, 2-H), 4.12 (dq, J=14.0, 7.5 Hz, 3H, Eta), 4.11 (dq, J=14.0, 7.0 Hz, 3H, Eta), 1.78-1.71 (m, 2H, 3-H), 1.32-1.28 (m, 2H, 4-H), 1.16 (dd, J=7.5, 7.0 Hz, 3H, Eta), 0.81 (t, J=7.5 Hz, 3H, 5-H);13C NMR (CDCl3): δ172.1, 170.1, 138.4, 138.3, 128.7, 128.6, 128.4, 127.3, 127.2, 120.4, 72.9, 61.2, 56.8, 33.0, 18.3, 14.0, 13.5;HR MS: calcd for C21H24O4Na (M+Na+) 363.1567. found 363.1569.(Entry 30)Methyl (S)-lactate1H NMR (CDCl3): δ4.24 (q, J=7.0 Hz, 1H, 2-H), 3.72 (s, 3H, MeO), 3.16 (br s, 1H, OH), 1.36 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): δ176.0, 66.6, 52.3, 20.2.Methyl (R)-2-(diphenylacetyloxy)propanoateHPLC (CHIRALCEL AD-H, i-PrOH/hexane=1/50, flow rate=0.75 mL/min): tR=16.4 min (98.3%), tR=19.7 min (1.7%);IR (neat): 1744, 1496, 1454, 748, 699 cm-1;1H NMR (CDCl3): δ7.28-7.20 (m, 8H, Ph), 7.19-7.13 (m, 2H, Ph), 5.07 (q, J=7.0 Hz, 1H, 2-H), 5.03 (s, 1H, 2'-H), 3.60 (s, 3H, MeO), 1.37 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): δ171.9, 170.9, 138.3, 138.2, 128.7, 128.63, 128.55, 128.4, 127.3, 127.2, 69.2, 56.6, 52.2, 16.8;HR MS: calcd for C18H18O4Na (M+Na+) 321.1097. found 321.1091.

Reference： [1]Shiina, Isamu; Nakata, Kenya; Ono, Keisuke; Sugimoto, Masuhiro; Sekiguchi, Akihiro [Chemistry - A European Journal, 2010, vol. 16, # 1, p. 167 - 172]
[2]Current Patent Assignee: TOKYO UNIVERSITY OF SCIENCE - US2011/319650, 2011, A1 Location in patent: Page/Page column 11

36
ethyl 2-hydroxy-n-valerate [ No CAS ]
[ 117-34-0 ]
[ 1208982-46-0 ]
[ 115626-59-0 ]
[ 88945-70-4 ]

Yield	Reaction Conditions	Operation in experiment
47%	With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h; Inert atmosphere; Resolution of racemate; optical yield given as %ee; enantioselective reaction;
1: 89 % ee 2: 47%	With 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h;	5 Test Example 5Production of Optically Active 2-Hydroxy Ester Using Various Types of Racemic 2-Hydroxy Ester (3) As shown in the above reaction scheme, to diethyl ether (0.2 M) containing 0.6 equivalents of pivalic acid anhydride and 0.5 equivalents of diphenylacetic acid were added 1.2 equivalents of diisopropyl ethylamine, 5% by mole of (+)-benzotetramisole (BTM), and a solution containing 1 equivalent of a racemic 2-hydroxy ester in diethyl ether at room temperature in this order, and this reaction mixture was stirred at room temperature for 12 hrs. Thereafter, the reaction was stopped with a saturated aqueous sodium bicarbonate solution. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether three to five times. After the organic layers were admixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to afford a corresponding diester and unreacted optically active 2-hydroxy ester. The results are shown in Table 5. TABLE 5 Yield [%] [a] cc [%] No.R5 R6 5a; 5b 5a; 5b s 29 Et n-Pr 47; 47 97; 89 217 30 Me Me 47; 23 97; 68 119 [a] Isolation yieldAs is seen from Table 5, prominently high enantiomeric excess ee and reaction velocity ratio s were exhibited also when a material other than the benzyl ester was used (Entries 29 and 30).The physical properties of the optically active hydroxy esters and the diesters in Table 5 are shown below.(Entry 29)Ethyl (S)-2-hydroxypentanoate1H NMR (CDCl3): δ4.19 (dq, J=14.0, 7.0 Hz, 1H, Eta), 4.18 (dq, J=14.0, 7.5 Hz, 1H, Eta), 2.96 (br d, J=3.5 Hz, 1H, OH), 1.75-1.65 (m, 1H, 3-H), 1.62-1.52 (m, 1H, 3-H), 1.48-1.30 (m, 2H, 4-H), 1.24 (dd, J=7.5, 7.0 Hz, 3H, Eta), 0.89 (t, J=7.3 Hz, 3H, 5-H);13C NMR (CDCl3): δ175.3, 70.2, 61.4, 36.4, 17.9, 14.1, 13.6.Ethyl (R)-2-(diphenylacetyloxy)pentanoateHPLC (CHIRALCEL AD-H, i-PrOH/hexane=1/50, flow rate=1.0 mL/min): tR=15.0 min (1.4%), tR=17.5 min (98.6%);IR (neat): 1745, 1496, 1454, 745, 701 cm-1;1H NMR (CDCl3): δ7.33-7.17 (m, 10H, Ph), 5.08 (s, 1H, 2'-H), 4.98 (dd, J=7.0, 6.0 Hz, 1H, 2-H), 4.12 (dq, J=14.0, 7.5 Hz, 3H, Eta), 4.11 (dq, J=14.0, 7.0 Hz, 3H, Eta), 1.78-1.71 (m, 2H, 3-H), 1.32-1.28 (m, 2H, 4-H), 1.16 (dd, J=7.5, 7.0 Hz, 3H, Eta), 0.81 (t, J=7.5 Hz, 3H, 5-H);13C NMR (CDCl3): δ172.1, 170.1, 138.4, 138.3, 128.7, 128.6, 128.4, 127.3, 127.2, 120.4, 72.9, 61.2, 56.8, 33.0, 18.3, 14.0, 13.5;HR MS: calcd for C21H24O4Na (M+Na+) 363.1567. found 363.1569.(Entry 30)Methyl (S)-lactate1H NMR (CDCl3): δ4.24 (q, J=7.0 Hz, 1H, 2-H), 3.72 (s, 3H, MeO), 3.16 (br s, 1H, OH), 1.36 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): δ176.0, 66.6, 52.3, 20.2.Methyl (R)-2-(diphenylacetyloxy)propanoateHPLC (CHIRALCEL AD-H, i-PrOH/hexane=1/50, flow rate=0.75 mL/min): tR=16.4 min (98.3%), tR=19.7 min (1.7%);IR (neat): 1744, 1496, 1454, 748, 699 cm-1;1H NMR (CDCl3): δ7.28-7.20 (m, 8H, Ph), 7.19-7.13 (m, 2H, Ph), 5.07 (q, J=7.0 Hz, 1H, 2-H), 5.03 (s, 1H, 2'-H), 3.60 (s, 3H, MeO), 1.37 (d, J=7.0 Hz, 3H, 3-H);13C NMR (CDCl3): δ171.9, 170.9, 138.3, 138.2, 128.7, 128.63, 128.55, 128.4, 127.3, 127.2, 69.2, 56.6, 52.2, 16.8;HR MS: calcd for C18H18O4Na (M+Na+) 321.1097. found 321.1091.

Reference： [1]Shiina, Isamu; Nakata, Kenya; Ono, Keisuke; Sugimoto, Masuhiro; Sekiguchi, Akihiro [Chemistry - A European Journal, 2010, vol. 16, # 1, p. 167 - 172]
[2]Current Patent Assignee: TOKYO UNIVERSITY OF SCIENCE - US2011/319650, 2011, A1 Location in patent: Page/Page column 11

37
[ 117-34-0 ]
[ 2051-96-9 ]
[ 1208982-31-3 ]
[ 56777-24-3 ]
benzyl (R)-Lactate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h; Inert atmosphere; Resolution of racemate; optical yield given as %ee; enantioselective reaction;
1: 82 % ee 2: 44%	With 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h;	2 Test Example 2Production of Optically Active 2-Hydroxy Ester Using Various Types of Carboxylic Acid Anhydride As shown in the above reaction scheme, to dichloromethane (0.2 M) containing 0.6 equivalents of carboxylic acid anhydride and 0.5 equivalents of diphenylacetic acid were added 1.2 equivalents of diisopropyl ethylamine, 5% by mole of (+)-benzotetramisole (BTM), and a solution containing 1 equivalent of racemic benzyl lactate in dichloromethane at room temperature in this order, and this reaction mixture was stirred at room temperature for 12 hrs. Thereafter, the reaction was stopped with a saturated aqueous sodium bicarbonate solution. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether three to five times. After the organic layer was mixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to afford a corresponding diester and unreacted optically active benzyl lactate. The results are shown in Table 2. TABLE 2 No.R2 Yield [%] of 2a[a] 2a /2c[b] Yield [%] of 2b[a] ee (2a;2b) [%] s 8 Ph 46 87/13 43 92;84 64 94-Me0C6H4 35 80/20 48 95;62 70 10 t-Bu 44 98/2 55 94;68 62 11PhMe2C 27 98/2 43 95;75 92 12Ph2MoC 37 >99/<1 44 96;62 87 13Ph3C 11 >99/<1 75 97;12 7214[c] t-Bu 44 98/2 55 97;82 146 [a]Isolation yield[b]Determined by 1H NMR[c]Diethyl ether used in place of dichloromethaneAs is seen from Table 2, Test Example 2 in which diphenylacetic acid was used as the carboxylic acid exhibited a very high reaction velocity ratio s of no less than 62 for any of the carboxylic acid anhydrides of Entries 8 to 14 used. Also, when a bulky carboxylic acid anhydride such as pivalic acid anhydride was used, the amount of the by-product (compound 2c) was small (Entries 10 to 14), and particularly, when pivalic acid anhydride was used, a high yield was attained (Entries 10 and 14). Furthermore, when diethyl ether was used in place of dichloromethane, a prominently high reaction velocity ratio s was attained (Entry 14).
1: 50 % ee 2: 33%	With 1-phenyl-1-cyclopentanecarboxylic acid anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	4 Test Example 4Production of Optically Active 2-Hydroxy Ester Using Various Types of Racemic 2-Hydroxy Ester (2) As shown in the above reaction scheme, to a solution containing 0.50 equivalents of diphenylacetic acid and 0.60 equivalents of 1-phenyl-1-cyclopentanecarboxylic acid anhydride in dichloromethane were sequentially added 1.2 equivalents of diisopropyl ethylamine, 5% by mole of (+)-benzotetramisole ((+)-BTM), and the racemic 2-hydroxy ester at room temperature. This reaction mixture was then allowed to react at room temperature for 12 hrs, whereby a corresponding optically active ester and an unreacted 2-hydroxy ester were obtained. The results are shown in Table 4. TABLE 4 Yield [%] [a] ee [%] No. R 4 4a; 4b 4a; 4b s 27 Me 33; 58 97; 50 107 28 Et 31; 49 94; 52 58 [a] Isolation yieldAs is seen from Table 4, also when 1-phenyl-1-cyclopentanecarboxylic acid anhydride and diphenylacetic acid were used in combination in place of diphenylacetic acid anhydride, prominently high enantiomeric excess ee and reaction velocity ratio s were attained (Entries 27 and 28).The production method and the physical properties of the optically active hydroxy esters and the diesters presented in Table 4 are shown below.(Entry 27)To a solution containing 1-phenyl-1-cyclopentanecarboxylic acid anhydride (48.3 mg, 0.133 mmol) and diphenylacetic acid (23.6 mg, 0.111 mmol) in dichloromethane was added diisopropyl ethylamine (46.4 μL, 0.266 mmol) at room temperature. After this reaction mixture was stirred for 10 min, (+)-benzotetramisole (2.8 mg, 0.0111 mmol) and racemic benzyl lactate (35.7 μL, 0.222 mmol) were added thereto at room temperature. After this reaction mixture was stirred at room temperature for 12 hrs, saturated sodium bicarbonate water was added at room temperature to stop the reaction. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether five times. After the organic layer was mixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1), and a highly polar fraction was fractionated again on silica gel thin layer chromatography (developing solvent: benzene/ethyl acetate=9/1) to afford a corresponding diester (23.0 mg, 58%, 50% ee) and unreacted optically active benzyl lactate. Moreover, the poorly polar fraction was also fractionated on silica gel thin layer chromatography (developing solvent: hexane/diethyl ether=5/1) to afford a corresponding diester (7.6 mg, 33%, 97% ee) and unreacted optically active benzyl lactate.Benzyl (S)-lactate[α]D28=-10.0 (c 1.10, acetone);HPLC (CHIRALPAK OD-H, i-PrOH/hexane=1/50, flow rate=1.0 mL/min): tR=16.7 min (75.2%), tR=18.7 min (24.8%);1H NMR (CDCl3): δ7.42-7.31 (m, 5H, Ph), 5.22 (s, 2H, Bn), 4.33 (ddd, J=13.4, 6.9, 5.4 Hz, 1H, 2-H), 2.81 (d, J=5.4 Hz, 1H, OH), 1.44 (d, J=6.9 Hz, 3H, 3-H).Benzyl (R)-2-(2,2-diphenylacetyloxy)propanoate[α]D28=+34.6 (c 1.43, CHCl3);HPLC (CHIRALPAK OD-H, i-PrOH/hexane=2/3, flow rate=1.0 mL/min): tR=30.6 min (1.5%), tR=46.3 min (98.5%);1H NMR (CDCl3): δ7.41-7.20 (m, 15H, Ph), 5.24-5.13 (m, 3H, 2-H, Bn), 5.10 (s, 1H, 2'-H), 1.49 (d, J=7.2 Hz, 3H, 3-H).

Reference： [1]Shiina, Isamu; Nakata, Kenya; Ono, Keisuke; Sugimoto, Masuhiro; Sekiguchi, Akihiro [Chemistry - A European Journal, 2010, vol. 16, # 1, p. 167 - 172]
[2]Current Patent Assignee: TOKYO UNIVERSITY OF SCIENCE - US2011/319650, 2011, A1 Location in patent: Page/Page column 5-6
[3]Current Patent Assignee: TOKYO UNIVERSITY OF SCIENCE - US2011/319650, 2011, A1 Location in patent: Page/Page column 10-11

38
[ 117-34-0 ]
C₂₉H₃₇N₂O₃Pol [ No CAS ]
[ 29022-11-5 ]
[ 86123-10-6 ]
[ 188970-92-5 ]
C₆₈H₇₉N₈O₁₂Pol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1492 - 1495

39
[ 117-34-0 ]
[ 13500-53-3 ]
[ 1256282-35-5 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 5696 - 5704

40
[ 109-01-3 ]
[ 117-34-0 ]
[ 56230-67-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 2,2-diphenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1h; Stage #2: 1-methyl-piperazine In tetrahydrofuran at 0 - 20℃;	To a solution of CDI (0.77 g, 4.72 mmol) in dry THF (15 mL) was added diphenylacetic acid (1 g, 4.71 mmol). The reaction mixture was allowed to stir at room temperature for 1 hour after which time it was cooled to 0° C. and N-methylpiperazine (0.5 mL) in THF (10 mL) was added. The reaction mixture was left at room temperature for 16 hours with stirring. The reaction mixture was poured onto aqueous sodium hydrogen carbonate (50 mL) and dichloromethane (25 mL) was added. The organic layer was separated and the aqueous phase washed with dichloromethane (2×25 mL). The combined organic extracts were dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure.The product was recrystallised from acetone and isolated as white crystals in 88% yield.1H NMR (CDCl3): δ 1.79 (m, 2H, CH2); 2.06 (m, 2H, CH2); 2.18 (s, 3H, NCH3); 2.32 (m, 2H, CH2); 3.41 (m, 2H, CH2); 3.67 (m, 4H, CH2); 5.12 (s, 1H, C(O)CH); 7.14-7.34 (m, 10H, aromatic H).13C NMR (CDCl3): δ 42.1; 45.8; 54.5; 54.7; 54.9; 121.4; 126.5; 127.1; 128.4; 128.5; 128.6; 129.0; 134.9; 139.2; 170.5 (CO).ESIMS: m/z 295 (100%, [M+H]+); 296 (22%); 363 (16%).EIMS: m/z 294 (100%, M+); 251 (15%); 165 (74%); 127 (85%).HREIMS: m/z M+ 294.1731 (calculated for C19H22N2O 294.1732).Melting Point: 129.5-130.7° C.Infrared νmax (KBr): 1628 s, 1493 w, 1461 m, 1433 m, 1292 m, 1230 m, 1172 w, 1042 w, 745 w cm-1 Anal.: Calc. for C19H22N2O: C, 77.52, H, 7.53; N, 9.52. Found C, 77.19, H, 7.23; N, 9.45.

Reference： [1]Current Patent Assignee: NATIONAL UNIVERSITY OF SINGAPORE; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; MARITIME AND PORT AUTHORITY OF SINGAPORE - US2011/92518, 2011, A1 Location in patent: Page/Page column 11

41
[ 4208-64-4 ]
[ 117-34-0 ]
[ 1315309-11-5 ]
[ 4208-64-4 ]
[ 27948-61-4 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 147 - 149

42
[ 57605-95-5 ]
[ 117-34-0 ]
(R)-α-methyl-1-naphthalenemethyl diphenylacetate [ No CAS ]
(S)-α-methyl-1-naphthalenemethyl diphenylacetate [ No CAS ]
[ 15914-84-8 ]
[ 42177-25-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole; 2,2-dimethylpropanoic anhydride In diethyl ether at 20℃; for 12h; Resolution of racemate; optical yield given as %ee;

Reference： [1]Nakata, Kenya; Shiina, Isamu [Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 7092 - 7096]

43
[ 117-34-0 ]
[ 3319-15-1 ]
(R)-α-methyl-4-methoxyphenylmethyl diphenylacetate [ No CAS ]
(S)-α-methyl-4-methoxyphenylmethyl diphenylacetate [ No CAS ]
(S)-1-(4-Methoxyphenyl)ethanol [ No CAS ]
[ 1517-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-9-methyl-2-phenyl-9-hydro-2-imidazolino[1,2-a]benzimidazole; 2,2-dimethylpropanoic anhydride In diethyl ether at 20℃; for 12h; Resolution of racemate; optical yield given as %ee;

Reference： [1]Nakata, Kenya; Shiina, Isamu [Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 7092 - 7096]

44
[ 117-34-0 ]
[ 2051-96-9 ]
[ 93-97-0 ]
[ 1208982-31-3 ]
[ 56777-24-3 ]
[ 1208982-36-8 ]
benzyl (R)-Lactate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 84 % ee 2: 46%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	2 Test Example 2Production of Optically Active 2-Hydroxy Ester Using Various Types of Carboxylic Acid Anhydride As shown in the above reaction scheme, to dichloromethane (0.2 M) containing 0.6 equivalents of carboxylic acid anhydride and 0.5 equivalents of diphenylacetic acid were added 1.2 equivalents of diisopropyl ethylamine, 5% by mole of (+)-benzotetramisole (BTM), and a solution containing 1 equivalent of racemic benzyl lactate in dichloromethane at room temperature in this order, and this reaction mixture was stirred at room temperature for 12 hrs. Thereafter, the reaction was stopped with a saturated aqueous sodium bicarbonate solution. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether three to five times. After the organic layer was mixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to afford a corresponding diester and unreacted optically active benzyl lactate. The results are shown in Table 2. TABLE 2 No.R2 Yield [%] of 2a[a] 2a /2c[b] Yield [%] of 2b[a] ee (2a;2b) [%] s 8 Ph 46 87/13 43 92;84 64 94-Me0C6H4 35 80/20 48 95;62 70 10 t-Bu 44 98/2 55 94;68 62 11PhMe2C 27 98/2 43 95;75 92 12Ph2MoC 37 >99/<1 44 96;62 87 13Ph3C 11 >99/<1 75 97;12 7214[c] t-Bu 44 98/2 55 97;82 146 [a]Isolation yield[b]Determined by 1H NMR[c]Diethyl ether used in place of dichloromethaneAs is seen from Table 2, Test Example 2 in which diphenylacetic acid was used as the carboxylic acid exhibited a very high reaction velocity ratio s of no less than 62 for any of the carboxylic acid anhydrides of Entries 8 to 14 used. Also, when a bulky carboxylic acid anhydride such as pivalic acid anhydride was used, the amount of the by-product (compound 2c) was small (Entries 10 to 14), and particularly, when pivalic acid anhydride was used, a high yield was attained (Entries 10 and 14). Furthermore, when diethyl ether was used in place of dichloromethane, a prominently high reaction velocity ratio s was attained (Entry 14).

Reference： [1]Current Patent Assignee: TOKYO UNIVERSITY OF SCIENCE - US2011/319650, 2011, A1 Location in patent: Page/Page column 5-6

45
[ 117-34-0 ]
[ 2051-96-9 ]
[ 794-94-5 ]
[ 1208982-31-3 ]
[ 56777-24-3 ]
[ 1208982-34-6 ]
benzyl (R)-Lactate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 62 % ee 2: 35%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	1 Test Example 1Production of Optically Active 2-Hydroxy Ester Using Various Types of Carboxylic Acid As shown in the above reaction scheme, to dichloromethane (0.2 M) containing 0.6 equivalents of p-methoxybenzoic acid anhydride (PMBA) and 0.5 equivalents of carboxylic acid were added 1.2 equivalents of diisopropyl ethylamine, 5% by mole of (+)-benzotetramisole (BTM), and a solution containing 1 equivalent of racemic benzyl lactate in dichloromethane at room temperature in this order, and this reaction mixture was stirred at room temperature for 12 hrs. Thereafter, the reaction was stopped with a saturated aqueous sodium bicarbonate solution. After the organic layer was fractionated, the aqueous layer was extracted with diethyl ether three to five times. It is to be noted that for Entries 6 and 7, the aqueous layer was extracted with dichloromethane. After the organic layer was mixed, the mixture was dried over anhydrous sodium sulfate. The solution was filtered and thereafter vacuum concentrated. Thus obtained mixture was fractionated on silica gel thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to afford a corresponding diester and unreacted optically active benzyl lactate. The results are shown in Table 1.The enantiomeric excess ee was determined by an HPLC analytical method on a chiral column. Further, the reaction velocity ratio s was calculated based on the formula of: s=[ln(1-C) (ee of 1-product)]/[ln(1-C) (ee of 1+product)], according to a method of Kagan et al, (Top. Stereochem., 1988, 18, p. 249-330). TABLE 1 No.R1 Yield [%] of 1a[a] 1a /1c[b] Yield [%] of 1b[a] ee (1a;1b) [%] s 1Ph(CH2)2 33 86/14 54 80;42 14 2p-To1CH2 35 86/14 42 85;46 20 3 i-Pr 50 95/5 47 85;78 29 4 c-Hex 38 87/13 34 88;56 27 5Ph2CH 35 80/20 48 95;62 70 6(α-Np)2CH 8 84/16 86 94;6 35 7(β-Np)2CH 31 89/11 52 95;51 63 [a]Isolation yield[b]Determined by 1H NMRAs is seen from Table 1, when a carboxylic acid having a secondary carbon atom in the α-position like a carboxylic acid in which R1 is Ph(CH2)2 or p-TolCH2 was used, the reaction velocity ratio s was no greater than 20 in either case, which was not satisfactory (Entries 1 and 2). On the other hand, when a more bulky carboxylic acid having a tertiary carbon atom in the α-position was used, the reaction velocity ratio s was as high as no less than 27. Accordingly, optically active benzyl lactate was successfully obtained with high efficiency (Entries 3 to 7). In particular, when diphenylacetic acid was used as the carboxylic acid, all of the yield, the enantiomeric excess ee, and the reaction velocity ratio s were very high (Entry 5).

Reference： [1]Current Patent Assignee: TOKYO UNIVERSITY OF SCIENCE - US2011/319650, 2011, A1 Location in patent: Page/Page column 4-5

46
[ 117-34-0 ]
[ 1428548-66-6 ]
[ 1428548-67-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	3.D Step D: N-(2-(benzyloxymethyl)-4-hydroxypyrimidin-5-yl)-2.2-di^ (3-f) Step D: N-(2-(benzyloxymethyl)-4-hydroxypyrimidin-5-yl)-2.2-di^ (3-f) A mixture of compound 3-e (1.6 g, 6.9 mmol), 2,2-diphenylacetic acid (1.47 g, 6.9 mmol), DIEA (1.8g, 13.8mmol), and TBTU (2.7 g, 8.28 mmol) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was added with sat. NH4CI (50 mL), extracted with DCM (100 mL), washed with water (50 mL) and brine ((50 mL). The organic layer was concentrated and purified by column chromatography to afford the product as a white solid, 3-f (2.2 g, 76%). 1H NMR (300 MHz, CDCI3) ? 4.45 (s, 2H), 4.63 (s, 2H), 5.07 (s, 1H), 7.27-7.40 (m, 16H), LC-MS (M+H)+ 426.1
76%	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	3.D Step D: N-(2-n?enzyloxymethyl)-4-hydroxypyrimidin-5-yl)-2,2-diphenylacetamide (3-f) A mixture of compound 3-e (1.6 g, 6.9 mmol), 2,2-diphenylacetic acid (1.47 g, 6.9 mmol), DIEA (1.8g, 13.8mmol), and TBTU (2.7 g, 8.28 mmol) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was added with sat. NH4CI (50 mL), extracted with DCM (100 mL), washed with water (50 mL) and brine ((50 mL). The organic layer was concentrated and purified by column chromatography to afford the product as a white solid, 3-f (2.2 g, 76%). 1H NMR (300 MHz, CDCI3) δ 4.45 (s, 2H), 4.63 (s, 2H), 5.07 (s, 1H), 7.27-7.40 (m, 16H), LC-MS (M+H)+ 426.1

Reference： [1]Current Patent Assignee: ADVENT INTERNATIONAL CORPORATION; MERCK & CO INC - WO2013/40789, 2013, A1 Location in patent: Page/Page column 49-50
[2]Current Patent Assignee: ADVENT INTERNATIONAL CORPORATION; MERCK & CO INC - WO2013/43621, 2013, A1 Location in patent: Page/Page column 50

47
[ 117-34-0 ]
[ 79-50-5 ]
[ 1426302-75-1 ]
(S)-pantolactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 51% 2: 48%	With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine In diethyl ether at 20℃; for 12h; Inert atmosphere; enantioselective reaction;

Reference： [1]Nakata, Kenya; Gotoh, Kouya; Ono, Keisuke; Futami, Kengo; Shiina, Isamu [Organic Letters, 2013, vol. 15, # 6, p. 1170 - 1173]

48
[ 117-34-0 ]
[ 19444-84-9 ]
[ 1351453-88-7 ]
(S)-2-diphenylacetyloxy-γ-butyrolactone [ No CAS ]
[ 52079-23-9 ]
[ 19444-84-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1170 - 1173

49
[ 117-34-0 ]
[ 1538-75-6 ]
[ 19444-84-9 ]
[ 1351453-88-7 ]
(S)-2-diphenylacetyloxy-γ-butyrolactone [ No CAS ]
C₉H₁₄O₄ [ No CAS ]
[ 52079-23-9 ]
[ 19444-84-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1170 - 1173

50
[ 117-34-0 ]
[ 609-15-4 ]
[ 1434871-32-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 17h;
98%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 17h;
98%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 17h;	ethyl 2-(2,2-diphenylacetoxy)-3-oxobutanoate A solution of diphenylacetic acid (2.12 g, 10 mmol) and ethyl 2-chloroacetoacetate (1.88 g, 11 mmol) in dry DMF (5 mL) was treated with DIPEA (2 mL, 11 mmol) and stirred at ii I 7h. Ether (150 mL) was added and the solution was washed with 2M HC1, 1M NaHCO3, brine and dried over MgSO4. Removal of solvent gave a pale yellow oil 3.33 g, 98%. MS 363 [NNa]. ‘H NMR (400 MHz, CDC13): ö 7.39- 7.25 (m, 5H), 5.50 (s, 1H), 5.23 (s, IH), 4.24 (q, J= 7.2 Hz, 2H), 2.20 (s, 3H), 1.25 (t, J 7.2 Hz, 3H). ‘3C NMR (100 MHz, CDC13): 8 197.5, 171.1, 164.3, 137.8, 137.7, 128.7, 128.6, 127.54, 127.48, 78.2, 62.5, 56.4, 27.0, 13.9.

Reference： [1]Reid, Robert C.; Yau, Mei-Kwan; Singh, Ranee; Lim, Junxian; Fairlie, David P. [Journal of the American Chemical Society, 2014, vol. 136, # 34, p. 11914 - 11917]
[2]Reid, Robert C.; Yau, Mei-Kwan; Singh, Ranee; Hamidon, Johan K.; Lim, Junxian; Stoermer, Martin J.; Fairlie, David P. [Journal of Medicinal Chemistry, 2014, vol. 57, # 20, p. 8459 - 8470]
[3]Current Patent Assignee: THE UNIVERSITY OF QUEENSLAND - WO2013/67578, A1 Location in patent: Page/Page column 51

51
[ 117-34-0 ]
[ 1448679-25-1 ]
[ 1448679-27-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	8.4 Procedure for the preparation of Compound 16d To a solution of 16c (70.0 mg, 0.22 mmol) and diphenyl acetic acid (52.0 mg, 0.25 mmol) in DCM (5 mL) was added EDCI.HC1 (85.5 mg, 0.44 mmol) and DMAP (5 mol%) and the mixture was stirred at RT overnight, TLC (PE:EA=2: 1) showed that the starting material was consumed. The mixture was diluted with DCM and washed with saturated NaHC03solution, brine, dried over Na2S04 and concentrated in vacuo. Purification by silica column (PE: EA = 10: 1 to 5: 1) gave 16d (95 mg, 86%) as a yellow solid. LC-MS (Agilent): R, 3.53 min; m/z calculated for C3iH3 N403 [M+H]+ 509.2, [M+Na]+ 531.3, [M+H]+ 509.2, [M+Na]+ 531.2.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2013/110134, 2013, A1 Location in patent: Page/Page column 59-60

52
[ 117-34-0 ]
(5S,6R)-3-amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3 ,6-trifluorophenyl)piperidin-2-one [ No CAS ]
(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-aminium 2,2-diphenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.4%	Stage #1: (5S,6R)-3-amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3 ,6-trifluorophenyl)piperidin-2-one With 3,5-dichlorosalicyclaldehyde In Isopropyl acetate; water at 55 - 60℃; Inert atmosphere; Stage #2: 2,2-diphenylacetic acid In tetrahydrofuran at 55 - 60℃; for 20h;	2 (3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-aminium 2,2-diphenylacetate (25) To a mixture of crude material containing (5S,6R)-3-amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-2-one (24, 2.00 g, 5.88 mmol), prepared according to the same method as the previous example, and 3,5-dichloro-2-hydroxybenzaldehyde (0.011 g, 0.059 mmol) in isopropyl acetate (15.0 ml) at 55-60° C. under nitrogen was slowly added a solution of diphenylacetic acid (1.26 g, 5.88 mmol) in THF (10.0 ml) over 2 h. Upon completion of acid addition, a thick salt suspension was agitated at 55-60° C. for another 18 h and then was allowed to cool to ambient temperature. The salt was filtered and washed with isopropyl acetate. After drying at 60° C. in a vacuum oven with nitrogen purge for 8 hours, 25 (2.97 g, 91.4%) was obtained as crystals. 1H NMR (500 MHz, DMSO-d6): δ 7.48 (qd, J=9.4, 4.9 Hz, 1H), 7.32 (d, J=7.7 Hz, 4H), 7.25-7.26 (m, 4H), 7.19-7.17 (m, 3H), 6.79 (br, 3H), 4.95 (s, 1H), 4.67 (dq, J=15.3, 9.7 Hz, 1H), 3.81-3.79 (m, 3H), 3.62 (dd, J=11.6, 6.5 Hz, 1H), 2.66-2.62 (m, 1H), 2.25 (dd, J=12.9, 6.4 Hz, 1H), 1.11 (d, J=6.5 Hz, 3H); 13C NMR (100 MHz, DMSO-d6): δ 174.4, 171.8, 156.9 (ddd, J=244, 7.0, 2.5 Hz), 149.1 (ddd, J=249, 14.4, 8.5 Hz), 147.2 (ddd, J=246, 13.9, 3.2 Hz), 141.4, 129.0, 128.5, 126.7, 125.5 (q, J=281 Hz), 118.0 (dd, J=19.8, 13.8 Hz), 117.1 (dd, J=19.2, 10.6 Hz), 112.3 (ddd, J=26.1, 6.7, 3.3 Hz), 58.5, 57.1, 51.7, 44.8 (q, J=32.7 Hz), 35.3, 27.5 (br t, J=4.6 Hz), 14.5.
2.97 g	With 3,5-dichlorosalicyclaldehyde In tetrahydrofuran; Isopropyl acetate at 55 - 60℃; for 20h; Inert atmosphere;	2 (3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-aminium 2,2-diphenylacetate (25) To a mixture of crude material containing (5S,6R)-3-amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3 ,6-trifluorophenyl)piperidin-2-one (24, 2.00 g, 5.88 mmol), prepared according to the same method as the previous example, and 3,5-dichloro-2-hydroxybenzaldehyde (0.011 g, 0.059 mmol) in isopropyl acetate (15.0 ml) at 55-60 °C under nitrogen was slowly added a solution of diphenylacetic acid (1.26 g, 5.88 mmol) in THF (10.0 ml) over 2 h. Upon completion of acid addition, a thick salt suspension was agitated at 55-60 °C for another 18 h and then was allowed to cool to ambient temperature. The salt was filtered and washed with isopropyl acetate. After drying at 60 °C in a vacuum oven with nitrogen purge for 8 hours, 25 (2.97 g, 91.4%) was obtained as crystals. 1H NMR (500 MHz, DMSO-d6): ö 7.48 (qd, J 9.4, 4.9 Hz, 1 H), 7.32 (d, J 7.7 Hz, 4 H), 7.25-7.26 (m, 4 H), 7.19-7.17 (m, 3 H), 6.79 (br, 3H),4.95 (s, 1 H), 4.67 (dq,J= 15.3, 9.7 Hz, 1 H), 3.81-3.79 (m, 3 H), 3.62 (dd,J= 11.6, 6.5 Hz, 1 H), 2.66-2.62(m, 1 H), 2.25 (dd,J= 12.9, 6.4 Hz, 1 H), 1.11 (d,J= 6.5 Hz, 3 H); 13CNMR (100 MHz, DMSO-d6): ö 174.4, 171.8, 156.9 (ddd, J= 244, 7.0, 2.5 Hz), 149.1 (ddd, J 249, 14.4, 8.5 Hz), 147.2 (ddd, J= 246, 13.9, 3.2 Hz), 141.4, 129.0, 128.5, 126.7, 125.5 (q, J 281 Hz), 118.0 (dd,J= 19.8, 13.8 Hz), 117.1 (dd,J 19.2, 10.6 Hz), 112.3 (ddd,J26.1, 6.7, 3.3 Hz), 58.5, 57.1, 51.7, 44.8 (q,J= 32.7 Hz), 35.3, 27.5 (brt,J= 4.6 Hz), 14.5.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2016/130273, 2016, A1 Location in patent: Paragraph 0184; 0185
[2]Current Patent Assignee: MERCK & CO INC - WO2013/169348, 2013, A1 Location in patent: Page/Page column 59; 60

53
[ 117-34-0 ]
[ 76456-06-9 ]
[ 1548754-56-8 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 968 - 971

54
[ 117-34-0 ]
[ 76456-06-9 ]
[ 1548753-38-3 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 968 - 971

55
[ 117-34-0 ]
[ 333-20-0 ]
[ 573659-19-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 2,2-diphenylacetic acid With trichloroisocyanuric acid; triphenylphosphine In toluene at 0℃; for 0.25h; Stage #2: potassium thioacyanate In toluene at 0 - 20℃; for 1.5h;	Preparation of Benzoyl Isothiocyanate from Benzoic Acid General procedure: To a cold solution of triphenylphosphine (0.262 g, 1 mmol) in toluene (3 mL), trichloroisocyanuric acid (0.069 g, 0.3 mmol) was added with continuous stirring. Benzoic acid (0.097 g, 0.8 mmol) was added and stirring was continued for 15 min. Potassium thiocyanate (0.193 g, 2 mmol) was added and the temperature was raised up to room temperature. Stirring was continued for 40 min at room temperature. The progress of the reaction was followed by TLC. Upon completion of the reaction, the concentrated residue passed through a short silica gel column using n-hexane / ethyl acetate mixture (vol. ratio: 60:1) as the eluent. Benzoyl isothiocyanate was obtained with 95 % yield after removing the solvent under reduced pressure.

Reference： [1]Entezari, Najmeh; Akhlaghinia, Batool; Rouhi-Saadabad, Hamed [Croatica Chemica Acta, 2014, vol. 87, # 3, p. 201 - 206]

56
[ 947-91-1 ]
[ 117-34-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	With diphenyl diselenide; dihydrogen peroxide; In water; at 20℃; for 6h;Green chemistry;	General procedure: Diphenyl diselenide (3, 0.006 g; 0.02 mmol) was treated with H2O2 (30%·w/w, 0.1 mL, 1 mmol) andwater (0.2 mL) and stirred at room temperature at 800 rpm until the discoloration of the reaction mixture;then, the aldehyde 1 (1 mmol) was added. After 6 h, the aqueous mixture was extracted three times withEtOAc (3 × 20 mL). The collected organic layers were dried over Na2SO4 and the solvent evaporatedunder reduced pressure.

Reference： [1]Molecules,2015,vol. 20,p. 10496 - 10510

57
[ 88017-70-3 ]
[ 117-34-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane In tetrahydrofuran; water at 20℃; for 2h; Inert atmosphere;	Microencapsulated Palladium Catalyzed Cleavage ofAllyl Esters; General Procedure: General procedure: A suspension of PdEnCat 30 (Aldrich; 0.4 mmol/g loading, 0.05 equiv) inTHF-H2O (9:1, 5 mL) was bubbled with argon for 10 min.After this time, DCHT (0.15 equiv) and the correspondingallyl ester 1 (1.0 equiv, 70 mg) were added under positivepressure. Finally, PhSiH3 was injected (2.0 equiv), and themixture was allowed to react for 2 h at r.t. under an argonatmosphere. After this time, the reaction was filtered throughCelite and the filtrate was evaporated under reducedpressure. The remaining solid was dissolved with EtOAc (20mL) and washed with H2O (3 × 10 mL) and brine (3 × 10mL). The organic layer was dried (MgSO4) and evaporatedunder vacuum. Purification by solid-phase extraction (C18reverse-phase chromatography, H2O/MeOH) gave purecarboxylic acids 2 (yields shown in Table 1). Purity wasdetermined by HPLC, 1H NMR and 13C NMR analyses. Allthe carboxylic acids are commercially available. Therecorded 1H and 13C NMR spectra of the synthesizedcompounds were consistent with those registered forcommercial samples.

Reference： [1]Pérez-López, Ana M.; González-Calderón, Dávir; Occorso, Antonio; Galindo-Ángel, Javier; Domínguez-Seglar, José F.; Tamayo, Juan A.; Díaz-Gavilán, Mónica; Gómez-Vidal, José A. [Synlett, 2014, vol. 25, # 16, p. 2319 - 2322]

58
[ 117-34-0 ]
[ 168466-85-1 ]
(1R,3R)-1-benzyl-3-(2,2-diphenylacetamido)-1-methylpiperidin-1-ium iodide [ No CAS ]
(1S,3R)-1-benzyl-3-(2,2-diphenylacetamido)-1-methylpiperidin-1-ium iodide [ No CAS ]

Reference： [1]Patent: WO2015/181837,2015,A2

59
[ 117-34-0 ]
[ 168466-85-1 ]
C₂₆H₂₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20.0℃;	Step 1: To a stirred solution of [17] (0.08g, 0.42mmol) in DMF (5.0ml) was added EDC (0.12g, 0.63 mmol), HOBT (0.08g, 0.63mmol) at room temperature. After an additional stirring for 5 minutes at same temperature, [16](0.08g, 0.42mmol) and NMM (0.14ml, 2.3mmol) was added. The reaction temperature was allowed to stir at room temperature for overnight. TLC showed complete consumption of starting material. Water (100 ml) was added and organic layer was extracted with ethyl acetate (2 x 100 ml). The combined organic layers were washed with water, brine and dried over sodium sulphate. The organic layer was concentrated to afford light brown sticky which was subjected to column chromatography with 1% MeOH/DCM as eluent to afford off white solid material[18] (0.1 lg, 68%). Analytical Data: [18] ESIMS: 385 [M++l ].

Reference： [1]Patent: WO2015/181837,2015,A2 .Location in patent: Page/Page column 44

60
[ 5831-77-6 ]
[ 117-34-0 ]
[ 88017-70-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 2-allyloxypyridine; 2,2-diphenylacetic acid With methyl trifluoromethanesulfonate In toluene at 0 - 23℃; for 1h; Inert atmosphere; Stage #2: With potassium carbonate In toluene for 1h; Reflux; Inert atmosphere;	General Procedure for the formation of allyl esters General procedure: A 5-mL reaction vial was equipped with a stir bar, a rubber septum, and an argon inlet needle. The vial was charged with allyloxypyridine (2) (1.1 equiv), carboxylic acid (4) (1.0 equiv), and dry PhCH3 (2.5 mL), and was allowed to stir at 0 °C. MeOTf (1.1 equiv) was added dropwise to the reaction mixture over 2min. Upon complete addition, the ice bath was removed and the reaction was allowed to stir for 1h or until 2 was completely consumed as indicated by TLC. The septum was quickly replaced with a reflux condenser fitted with an N2 inlet adapter. The reaction mixture was heated at reflux (oil bath 115 °C), and K2CO3 (0.95 equiv) was added in one portion through the top of the reflux condenser. Upon complete consumption of the carboxylic acid as indicated by TLC (typically 1-2 h), the mixture was diluted with ethyl acetate (10 mL). The diluted reaction mixture was washed with water (10 mL), followed by brine (10 mL). The organic fraction was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to isolate the crude product mixture. The crude mixture was purified by flash chromatography to yield the allyl ester product (5).

Reference： [1]Strayer, Timothy A.; Culy, Caleb C.; Bunner, Matthew H.; Frank, Amie R.; Albiniak, Philip A. [Tetrahedron Letters, 2015, vol. 56, # 48, p. 6807 - 6809]

61
[ 117-34-0 ]
[ 4695-14-1 ]
C₂₇H₂₃NO [ No CAS ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 784 - 787

62
[ 117-34-0 ]
[ 4695-14-1 ]
C₂₃H₁₉NO [ No CAS ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 784 - 787

63
[ 117-34-0 ]
[ 2216-68-4 ]
C₂₅H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 15h;Inert atmosphere;	General procedure: A solution of diphenylacetic acid (212 mg, 1.0 mmol), N-methylaniline (128 mg, 1.2mmol), DCC (247 mg, 1.2 mmol), and DMAP (24 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 15 h. After aqueous extractive workup and column chromatographic purification process (hexanes/Et2O,5:1) 1a was obtained as a white solid, 226 mg (75%). Other 2,2,N-triarylacetamides were prepared similarly from corresponding N-arylaminesand 2,2-diarylacetic acids. Diphenylacetic acid, bis(4-chlorophenyl)acetic acid and 9-fluorenecarboxylic acid were purchased from commercial sources, and other diarylacetic acids were prepared by Friedel-Crafts reaction of arenes and corresponding mandelic acid derivatives according to the reported methods.3,4

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 784 - 787

64
[ 117-34-0 ]
[ 2216-68-4 ]
C₂₅H₁₉NO [ No CAS ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 784 - 787

65
[ 4597-87-9 ]
[ 117-34-0 ]
N-methyl-2,2-diphenyl-N-(pyridine-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; Inert atmosphere;	Typical procedure for the preparation of 1a General procedure: A solution of diphenylacetic acid (212 mg, 1.0 mmol), N-methylaniline (128 mg, 1.2mmol), DCC (247 mg, 1.2 mmol), and DMAP (24 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 15 h. After aqueous extractive workup and column chromatographic purification process (hexanes/Et2O,5:1) 1a was obtained as a white solid, 226 mg (75%). Other 2,2,N-triarylacetamides were prepared similarly from corresponding N-arylaminesand 2,2-diarylacetic acids. Diphenylacetic acid, bis(4-chlorophenyl)acetic acid and 9-fluorenecarboxylic acid were purchased from commercial sources, and other diarylacetic acids were prepared by Friedel-Crafts reaction of arenes and corresponding mandelic acid derivatives according to the reported methods.3,4
58%	Stage #1: 2,2-diphenylacetic acid With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0℃; for 0.5h; Stage #2: With dmap In dichloromethane at 20℃; for 0.166667h; Stage #3: 2-(N-methylamino)pyridine With triethylamine In dichloromethane at 20℃; for 1h;	General procedure for synthesis of N-methyl-2-amino pyridine amides General procedure: A. To a mixture of benzoic acid (50 mg, 0.41 mmol, 1 equiv), PPh3 (160 mg, 0.61 mmol, 1.5 equiv) and NBS (108.5 mg, 0.61 mmol, 1.5 equiv), CH2Cl2 (1.5 ml) was added and the reaction was stirred at 0 °C for 30 min. Thereaction was brought to room temperature and DMAP (10 mg, 0.08 mmol, 0.20 equiv) was added and stirred for 10 min. The mixture of N-methyl-2-amino pyridine (49 mg, 0.45 mmol, 1.1 equiv), Et3N (45.5 mg, 63 µl, 0.45 mmol, 1.1 equiv) and CH2Cl2 (0.5 ml) were added and the reaction was stirred for1 h at room temperature. The reaction mixture was diluted with EtOAc and washed with aqueous sodium bicarbonate solution. The bicarbonate washings were again extracted with EtOAc and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure.Column chromatography was performed using EtOAc/Petroleum ether (1:5).

Reference： [1]Lim, Jin Woo; Kim, Ko Hoon; Moon, Hye Ran; Kim, Jae Nyoung [Tetrahedron Letters, 2016, vol. 57, # 7, p. 784 - 787]
[2]Pilathottathil, Fathima; Vineet Kumar, Doppalapudi; Kaliyamoorthy, Alagiri [Synthetic Communications, 2020, vol. 50, # 11, p. 1622 - 1632]

66
[ 589-09-3 ]
[ 117-34-0 ]
C₂₃H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; Inert atmosphere;	Typical procedure for the preparation of 1a General procedure: A solution of diphenylacetic acid (212 mg, 1.0 mmol), N-methylaniline (128 mg, 1.2mmol), DCC (247 mg, 1.2 mmol), and DMAP (24 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 15 h. After aqueous extractive workup and column chromatographic purification process (hexanes/Et2O,5:1) 1a was obtained as a white solid, 226 mg (75%). Other 2,2,N-triarylacetamides were prepared similarly from corresponding N-arylaminesand 2,2-diarylacetic acids. Diphenylacetic acid, bis(4-chlorophenyl)acetic acid and 9-fluorenecarboxylic acid were purchased from commercial sources, and other diarylacetic acids were prepared by Friedel-Crafts reaction of arenes and corresponding mandelic acid derivatives according to the reported methods.3,4

Reference： [1]Lim, Jin Woo; Kim, Ko Hoon; Moon, Hye Ran; Kim, Jae Nyoung [Tetrahedron Letters, 2016, vol. 57, # 7, p. 784 - 787]

67
C₂₂H₂₀O₄ [ No CAS ]
[ 117-34-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With iron(III) chloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Green chemistry;	Deprotection of 2,4-DMPM-Protected Ester (6) General procedure: To a solution of the 2,4-DMPM ester (0.2 mmol) in CH2Cl2 (1 mL) was added FeCl3(0.01 mmol), then stirred at room temperature under argon. After being stirred until the reaction was completed, the reaction mixture was directly filtrated through a small amount of a silica-gel pad and washed with Et2O. The filtrate was concentrated in vacuoto give the sufficiently-pure carboxylic acid. When some peaks derived from undetermined side-products were observed in the 1H-NMR spectra, the analytically-pure deprotected carboxylic acid was obtained after the normal silica-gel column chromatography (Table 3).

Reference： [1]Sawama, Yoshinari; Masuda, Masahiro; Honda, Akie; Yokoyama, Hiroki; Park, Kwihwan; Yasukawa, Naoki; Monguchi, Yasunari; Sajiki, Hironao [Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 778 - 784]

68
[ 117-34-0 ]
methyl piperidine-4-acetate hydrochloride [ No CAS ]
methyl 2-(1-(2,2-diphenylacetyl)piperidin-4-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 5.5h;	9 methyl 2-(1-(2,2-diphenylacetyl)piperidin-4-yl)acetate diphenylaceticacid (1.21g, 5.16mmol) in DMF (10.0mL) solution of diisopropylethylamine (1.98mL, 11.4mmol),HATU (2.16g, 5.68mmol) and 2(piperidine 4yl)acetate hydrochloride (1.00 g, 2.58 mmol) was added at roomtemperature and stirred for 5.5 hours at the same temperature. Water was added to the reaction mixture, and the mixture was extracted with nhexane/ethyl acetate = 1/4. The organic layer was dried over anhydrous sodium sulfate, filtered, andthe filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, nhexane/ ethyl acetate = 90 / 1055/ 45) to give 2(1(2,2diphenylacetyl)piperidin4yl)methyl acetate (hereinafter ,obtained reference example compound of 9) (1.73g, 4.92mmol, 95.4%) as a colorless oil.

Reference： [1]Current Patent Assignee: TORAY INDUSTRIES INC - JP2015/124178, 2015, A Location in patent: Paragraph 0129

69
[ 1016876-42-8 ]
[ 117-34-0 ]
2-(1-(2,2-diphenylacetyl)piperidin-4-yl)-N-phenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 15h;	1 Synthesis of 2-(1-(2,2-diphenylacetyl)piperidin-4-yl)-N-phenylacetamide Diphenylaceticacid (3.15g, 14.8mmol) in DMF (24.0mL) solution of diisopropylethylamine (3.24mL,18.6mmol), HATU (5.64g, 14.8mmol) and N-phenyl-2-(piperidin-4yl)acetamide (2.70 g) was added at room temperature and stirred for 15 hours at the same temperature. Water was added to the reaction mixture, and the mixture was extracted with n-hexane/ethyl acetate = 1/4. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, nhexane/ ethyl acetate = 90/10 to 50/50), 2-(1-(2,2-diphenylacetyl)piperidin-4-yl)-N-phenylacetamide(hereinafter, the compound of example 1) (1.73g, 4.92mmol, 95.4%) was obtained as a white solid.

Reference： [1]Current Patent Assignee: TORAY INDUSTRIES INC - JP2015/124178, 2015, A Location in patent: Paragraph 0116

70
[ 117-34-0 ]
N-tert-butyl-N'-phenyl-S-phenylisothiourea [ No CAS ]
[ 4695-14-1 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4602 - 4605

71
2-(diphenylmethoxy)-pyridine [ No CAS ]
[ 117-34-0 ]
[ 13144-31-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 12h;	General procedure for the preparation of DPM ester compounds (5a-5s) General procedure: To a solution of benzoic acid (0.122 g. 1.00 mmol) and 2-diphenylmethoxypyridine (0.39 g, 1.50 mmol) in DCE (2 mL) FeCl3 (0.0048 g. 0.03 mmol) was added. The mixture was stirred at room temperature for 12 h. The reaction mixture was extracted with ethyl acetate (210 mL), and then washed with water (10 mL), followed by brine (10 mL).The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was then purified using flash column chromatography on silica gel with hexane-CH2Cl2 as eluent to afford the desired product 5a as a white solid (0.271 g, 94%).
91%	With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at 20℃; for 6h; Inert atmosphere;	2.2. General procedure of the synthesis of Diphenylmethyl esters (5a-5x): General procedure: To a solution of benzoic acid (0.12 g. 1.00 mmol) and 2-diphenylmethoxypyridine (0.39 g, 1.50 mmol) in DCE (4 mL) BF3OEt2 (0.028 g. 0.20 mmol) was added. The mixture was stirred at room temperature for 6h. The reaction mixture was extracted with ethyl acetate (2 x 10 mL), and then washed with water (10 mL), followed by brine (10 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with hexane-CH2Cl2 as eluent to afford the desired product 5a as a white solid (0.175 g, 95%)

Reference： [1]Tran, Van Hieu; La, Minh Thanh; Kim, Hee-Kwon [Synthetic Communications, 2019, vol. 49, # 18, p. 2379 - 2387]
[2]La, Minh Thanh; Kim, Hee-Kwon [Tetrahedron Letters, 2018, vol. 59, # 19, p. 1855 - 1859]

72
[ 117-34-0 ]
1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-2-(methylamino)butan-1-one [ No CAS ]
N-(1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutan-2-yl)-N-methyl-2,2-diphenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Inert atmosphere;	4 Example 4: Synthesis of N-(1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutan-2-yl)-N-methyl-2,2-diphenylacetamide Add to a solution of 2,2-diphenylacetic acid (1.55 g, 7.3 mmol) and pyridine (1.0 mL, 12.4 mmol) in 20 mL anhydrous dichloromethane at 25 °C and N2 Cyclohexylcarbodiimide DCC (2.02 g, 9.8 mmol). After stirring for 5 minutes, 1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-2-(methylamino)butan-1-one (0.7 g, 2.11 was added) 20 mL anhydrous dichloromethane solution, The mixture was stirred overnight. TLC (95:5 in dichloromethane: methanol containing 2% ammonia) was found to be complete. The reaction was quenched with saturated aqueous sodium bicarbonate and filtered over EtOAc. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried with EtOAc (EtOAc m.1.2 g of a light brown solid were obtained. The crude product was purified by flash column chromatography. Purification was performed using a gradual gradient of 2% to 8% of ΜeOΗ:dichloromethane and 2% ammonia. The pure product was obtained and treated with 1.0 mol/L HCl in diethyl ether. Obtaining N-(1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutan-2-yl)-N-methyl-2,2-diphenylacetamide 0.98g, yield 88%
88%	With pyridine; dicyclohexyl-carbodiimide In dichloromethane at 25℃; Inert atmosphere;	4 Embodiment 4: N-{1-[4-(bromomethyl)piperidin-1-yl]-4,4,4-trifluoro-1-oxobutan-2-yl}-N-methyl-2,2-diphenylacetamide synthesis In the 25 °C and N2The lower, to the 2, 2 - diphenyl acetic acid (1.55 g, 7.3 mmol) and pyridine (1.0 ml, 12.4 mmol) in 20 ml anhydrous dichloromethane solution by adding 1, 3 - dicyclohexyl carbodiimide DCC (2.02 g, 9.8 mmol). Stirring 5 minutes, add 1-[4-(bromomethyl)piperidin-1-yl]-4,4,4-trifluoro-2-(methylamino)butan-1-one(0.7 g, 2 . 11 mmol) in 20 ml anhydrous dichloromethane solution, and the mixture is stirred overnight. TLC (95:5 of the dichloromethane: containing 2% ammonia methanol) detecting the completion of reaction. Saturated sodium bicarbonate solution for quenching the reaction and the diatomite filter, separating, the aqueous layer dichloromethane is used for extraction. The combined organic layer using Na2SO4After drying, filtering and vacuum concentrated, to obtain 1.2 g light brown solid. The crude product through rapid column chromatography, using 2% -8% of MeOH: dichloromethane and 2% ammonia gradient purification step, to obtain the pure product, then 1.0 µM/LHCl of ethyl ether solution processing, to obtain N-{1-[4-(bromomethyl)piperidin-1-yl]-4,4,4-trifluoro-1-oxobutan-2-yl}-N-methyl-2,2-diphenylacetamide0.98 g, yield is 88%
88%	Stage #1: 2,2-diphenylacetic acid With dicyclohexyl-carbodiimide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: 1-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-2-(methylamino)butan-1-one In dichloromethane	4 Example 4: N-(1-(4-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutan-2-yl)-N-methyl- Synthesis of 2,2-diphenylacetamide Add to a solution of 2,2-diphenylacetic acid (1.55 g, 7.3 mmol) and pyridine (1.0 mL, 12.4 mmol) in 20 mL anhydrous dichloromethane at 25 ° C and N.1,3-Dicyclohexylcarbodiimide DCC (2.02 g, 9.8 mmol). After stirring for 5 minutes,Add 1-mL-(4-(bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-2-(methylamino)butan-1-one (0.7 g, 2.11 mmol) in 20 mL Water dichloromethane solution,The mixture was stirred overnight. TLC (95:5 in dichloromethane: methanol containing 2% ammonia) was found to be complete.The reaction was quenched with EtOAc (EtOAc m. The combined organic layers were dried with EtOAc EtOAc m. The crude product was purified by flash column chromatography eluting with EtOAc EtOAc:EtOAcN-(1-(4-(Bromomethyl)piperidin-1-yl)-4,4,4-trifluoro-1-oxobutan-2-yl)-N-methyl-2,2- Diphenylacetamide 0.98g, yield 88%,

Reference： [1]Current Patent Assignee: Tian Yuanqiang - CN107987012, 2018, A Location in patent: Paragraph 0008; 0016
[2]Current Patent Assignee: Tian Yuanqiang - CN108191839, 2018, A Location in patent: Paragraph 0010; 0030-0032
[3]Current Patent Assignee: Tian Yuanqiang - CN108250190, 2018, A Location in patent: Paragraph 0030; 0031; 0032

73
[ 524-38-9 ]
[ 117-34-0 ]
[ 63591-86-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
86%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h; Inert atmosphere;	A; D General Procedure for Ni-Catalyzed Decarboxylative Borylation of Alkyl Carboxylic Acids via in situ Generated RAEs (General Procedure D) General procedure: A screw-capped culture tube with a stir bar was charged with alkyl carboxylic acid (0.2 mmol), /V-hydroxyphthalimide or tetrachloro-/V-hydroxyphthalimide (0.2 mmol, 1 .0 equiv) and Λ/,Λ/'-dicyclohexylcarbodiimide (0.2 mmol, 1 .0 equiv). The tube was then evacuated and backfilled with argon for three times. CH2CI2 (2.0 mL) was added and the resulting mixture was stirred at room temperature for 2 h before the volatiles were removed in vacuo. MgBr2 - OEt2 (77 mg, 0.3 mmol, 1 .5 equiv) was added. The tube was evacuated and backfilled with argon for three times. Suspension A (0.8 mL, NiCI2 - 6H20 (10 mol%)/L1 (13 mol%) in THF) or suspension C (0.8 mL, NiCI2 - 6H20 (10 mol%)/L2 (13 mol%) was added. The mixture was stirred vigorously at room temperature for 15 min (or until no granular MgBr2 OEt2 was observed) and was subsequently cooled to 0 °C before a suspension of [B2pin2Me]Li in THF (1 .1 mL) was added in one portion (note: do not add it dropwise). After being strred for 1 h, the reaction was warmed to room temperature and stirred for another 1 h. The reaction mixture was then quenched with 0.1 N HCI (10 mL) and extracted with Et20 (5 mLx2). The combined organic layers were dried over Na2S04, concentrated in vacuo and purified by column chromatography to give the desired product.

Reference： [1]Zheng, Chao; Wang, Yuting; Xu, Yangrui; Chen, Zhen; Chen, Guangying; Liang, Steven H. [Organic Letters, 2018, vol. 20, # 16, p. 4824 - 4827]
[2]Current Patent Assignee: SCRIPPS RESEARCH - WO2018/175173, 2018, A1 Location in patent: Page/Page column 27; 38-39; 60

74
[ 117-34-0 ]
[ 83766-88-5 ]
[ 5350-81-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate; In toluene; at 20.0℃; for 0.5h;	Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3748 - 3754

75
[ 117-34-0 ]
[ 180683-64-1 ]
C₂₅H₃₂N₂O₃ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 2115 - 2128

76
[ 117-34-0 ]
[ 96402-49-2 ]
[ 125238-99-5 ]
N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid [ No CAS ]
diphenylacetyl-D-Dab-Dab-1-Nal-1-Nal-Dab-NH2 [ No CAS ]

Reference： [1]Biomacromolecules,2019,vol. 20,p. 2515 - 2529

77
[ 117-34-0 ]
[ 96402-49-2 ]
[ 125238-99-5 ]
N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid [ No CAS ]
diphenylacetyl-D-Dab-Dab-1-Nal-NH2 [ No CAS ]

Reference： [1]Biomacromolecules,2019,vol. 20,p. 2515 - 2529

78
[ 117-34-0 ]
[ 125238-99-5 ]
N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine [ No CAS ]
N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid [ No CAS ]
diphenylacetyl-D-Dab-Dab-2-Nal-NH2 [ No CAS ]

Reference： [1]Biomacromolecules,2019,vol. 20,p. 2515 - 2529

79
[ 117-34-0 ]
[ 96402-49-2 ]
[ 125238-99-5 ]
diphenylacetyl-Dab-Dab-1-Nal-NH2 [ No CAS ]

Reference： [1]Biomacromolecules,2019,vol. 20,p. 2515 - 2529

80
[ 117-34-0 ]
[ 1241977-01-4 ]
thieno[3,4-b]thiophen-2-ylmethyl 2-(cyclohexa-1,5-dien-1-yl)-2-phenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64.5%	Stage #1: 2,2-diphenylacetic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: thieno[3,4-b]thiophen-2-yl-methanol In dichloromethane for 24h;	General procedure: Then, the substituted monomers were synthesized by simpleesterification reaction at room temperature (Scheme 2). Moreprecisely,1.2 eq. of the corresponding carboxylic acid,1.2 eq. (130) gof N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide hydrochloride(130 mg) and 4-(dimethylamino)pyridine (DMAP) (20 mg)were added to 20 mL of absolute dichloromethane. After stirring for30 min,100mg of Thieno-OH (1eq.)was added to the mixture. Afterone day, the crude product was purified by columnchromatography.

Reference： [1]Sane, Omar; Diouf, Alioune; Pan, Miaobo; Morán Cruz, Gabriela; Savina; Méallet-Renault, Rachel; Dieng, Samba Yandé; Amigoni; Guittard, Frédéric; Darmanin, Thierry [Electrochimica Acta, 2019, vol. 320]

81
[ 762-04-9 ]
[ 117-34-0 ]
[ 27329-60-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With dipotassium peroxodisulfate; silver nitrate; In ethanol; at 50℃;	Add 2,2-diphenylacetic acid (212 mg, 1 mmol), diethyl phosphite (276 mg, 2 mmol), potassium persulfate (540 mg, 2.0 mmol), silver nitrate (34 mg, 0.2 mmol) and ethanol (10 mL) at 50 oC;TLC follows the reaction to completion;The crude product obtained after the reaction was separated by column chromatography (dichloromethane: methanol = 98: 2) to obtain the target product (yield 89%).

Reference： [1]Patent: CN110229188,2019,A .Location in patent: Paragraph 0046

82
[ 117-34-0 ]
[ 754-05-2 ]
C₁₉H₂₂O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With trans-bis(acetonitrile)palladium(II) chloride; silver(I) acetate In 1,2-dichloro-ethane at 40℃; for 8h;	15 Example 15 A method for preparing an aromatic vinyl silane compound includes the following steps: To a 25 mL reaction tube were added 0.1061 g of diphenylacetic acid, 0.22 mL of trimethylvinylsilane, 0.0130 g of bis (acetonitrile) palladium dichloride, and 0.2504 g of silver acetate, an additional 5 mL of dichloroethane was added. The reaction tube was moved to an oil bath at 40 ° C for 8 h. After flash column chromatography, the product was concentrated under reduced pressure with a yield of 62%.

Reference： [1]Current Patent Assignee: HANGZHOU NORMAL UNIVERSITY - CN110698507, 2020, A Location in patent: Paragraph 0078-0080

83
[ 96-31-1 ]
[ 117-34-0 ]
[ 954-21-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With magnesium(II) nitrate hexahydrate In octane at 130℃; for 24h;

Reference： [1]Blacker, A. John; Chhatwal, A. Rosie; Lomax, Helen V.; Marcé, Patricia; Williams, Jonathan M. J. [Chemical Science, 2020, vol. 11, # 22, p. 5808 - 5818]

84
[ 117-34-0 ]
N-[4-(3-aminopropoxy)-3,5-dibromophenethyl]-N-methylpropionamide [ No CAS ]
N-{3,5-dibromo-4-[3-(2,2-diphenylacetamido)propoxy]phenethyl}-N-methylpropionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2,2-diphenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.25h; Stage #2: N-[4-(3-aminopropoxy)-3,5-dibromophenethyl]-N-methylpropionamide In dichloromethane at 20℃; for 15h;	Analogues 4a-g; General Procedure General procedure: To a stirred solution of the corresponding acid (1 equiv) in anhydrous CH2Cl2 (1.5 mL) were added HOBt (32 mg, 0.24 mmol, 2 equiv) and EDC·HCl (45 mg, 0.24 mmol, 2 equiv). The resulting mixture was then stirred for 15 min at room temperature to give a clear solution. A solution of compound 6 (50 mg, 0.12 mmol, 1 equiv) in CH2Cl2 (1.5 mL) was added and the reaction mixture was then allowed to stir at room temperature for 11-20 h. The mixture was quenched by adding aqueous NaHCO3 solution (5 mL) and the aqueous layer was extracted with CH2Cl2 (3 × 15 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure.

Reference： [1]Hussain, Mulla Althafh; Khan, Faiz Ahmed; Shashi, Shashi [Synthesis, 2019, vol. 51, # 24, p. 4601 - 4610]

85
[ 117-34-0 ]
[ 6294-52-6 ]
N-(5,6-dimethoxybenzo[d]thiazol-2-yl)-2,2-diphenylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 48h;	General procedure: The respective carboxylic acid (1.0 eq.), TBTU (1.1 eq.), and HOBt were dissolved in dry DMF and DIPEA (4.0 eq.) was added while cooling with an ice-water bath. The corresponding amine (1.0 eq.) was added after 30 min and the solution was stirred for 2 d at r.t. Water and EtOAc were added and the aqueous phase was extracted three times with EtOAc and the combined organic phases were washed with 2 M HCl, saturated NaHCO3-solution, and saturated NaCl-solution three times each. The organic phase was dried with MgSO4 and the solvent was evaporated under reduced pressure.

Reference： [1]Bioorganic and Medicinal Chemistry,2021,vol. 47

86
[ 154350-29-5 ]
[ 117-34-0 ]
C₁₆H₁₇NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With Isobutyronitrile; copper(II) bis(trifluoromethanesulfonate); sodium phosphate; In dichloromethane; at 20℃; for 24h;Irradiation; Inert atmosphere; Sealed tube;	General procedure: An oven-dried 6-ml vial equipped witha stir bar was placed in a nitrogen-filled glovebox and charged with Cu(OTf)2 (180.8 mg, 2.5 equiv., 0.50 mmol), Na3PO4 (98.2 mg, 3.0 equiv., 0.60 mmol), the sulfonamide nucleophile (1.5-3.0 equiv.), carboxylic acid (1.0 equiv., 0.20 mmol), methylene chloride (2.0 ml, 0.10 M) and isobutyronitrile (100 μl, 5.5 equiv.,1.1 mmol). The vial was sealed with a screwcap bearing a Teflon septum, removed from the glovebox and placed on a stir plate. The vial was irradiated at 427 nm with two 40-W Kessil PR160 lamps at a distance of 10 cm with stirring at 800 r.p.m. A fan was used to maintain the vial at room temperature. After 24 h, the crude reaction mixture was diluted with 1.5 ml of EtOAc and adsorbed directly on diatomaceous earth (Celite). The product was purified by flash chromatography on silica gel, eluting with mixtures of ethyl acetate and hexanes.

Reference： [1]Nature Chemistry,2022,vol. 14,p. 94 - 99

87
[ 117-34-0 ]
dimethyl (1-benzylpiperidin-4-yl)carbonimidodithioate [ No CAS ]
1-(1-benzylpiperidin-4-yl)-4,4-bis(methylthio)-3,3-diphenylazetidin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: dimethyl (1-benzylpiperidin-4-yl)carbonimidodithioate With bis(trichloromethyl) carbonate In dichloromethane at 50℃; for 0.5h; Stage #2: 2,2-diphenylacetic acid With triethylamine In dichloromethane for 12h; Reflux;	4.1.6. 1-(1-Benzylpiperidin-4-yl)-4,4-bis(methylthio)-3,3-diphenylazetidin-2-one (13) Triphosgene (227 mg, 0.76 mmol) was added to a solution of 12(486 mg, 2.29 mmol) in dry DCM (9.3 mL); then, it was heated at 50 °C for 30 min. A solution of diphenylacetic acid (450 mg, 1.53 mmol) in dry DCM (9.3 mL) and TEA (640 μL, 4.59 mmol) were added to the reaction mixture and refluxed for 12 h. A satured solution of NaHCO3 was added slowly to the cooled mixture at rt and the compound was extracted with DCM (3 x 15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM:Acetone 40:1) to afford the title compound 13. Yellow oil, 52% yield. 1HNMR (300 MHz, CDCl3) δ 7.73 (d, J = 7.0 Hz, 4H), 7.42-7.20 (m, 11H),3.54 (s, 2H), 3.27 (dt, J = 19.8, 7.9 Hz, 1H), 3.00 (d, J = 11.7 Hz, 2H),2.66-2.46 (m, 2H), 2.11-1.92 (m, 4H), 1.73 (s, 6H); ESI-MS m/z: 489[M+H]+.
52%	Stage #1: dimethyl (1-benzylpiperidin-4-yl)carbonimidodithioate With bis(trichloromethyl) carbonate In dichloromethane at 50℃; for 0.5h; Stage #2: 2,2-diphenylacetic acid With triethylamine In dichloromethane for 12h; Reflux;	4.1.6. 1-(1-Benzylpiperidin-4-yl)-4,4-bis(methylthio)-3,3-diphenylazetidin-2-one (13) Triphosgene (227 mg, 0.76 mmol) was added to a solution of 12(486 mg, 2.29 mmol) in dry DCM (9.3 mL); then, it was heated at 50 °C for 30 min. A solution of diphenylacetic acid (450 mg, 1.53 mmol) in dry DCM (9.3 mL) and TEA (640 μL, 4.59 mmol) were added to the reaction mixture and refluxed for 12 h. A satured solution of NaHCO3 was added slowly to the cooled mixture at rt and the compound was extracted with DCM (3 x 15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM:Acetone 40:1) to afford the title compound 13. Yellow oil, 52% yield. 1HNMR (300 MHz, CDCl3) δ 7.73 (d, J = 7.0 Hz, 4H), 7.42-7.20 (m, 11H),3.54 (s, 2H), 3.27 (dt, J = 19.8, 7.9 Hz, 1H), 3.00 (d, J = 11.7 Hz, 2H),2.66-2.46 (m, 2H), 2.11-1.92 (m, 4H), 1.73 (s, 6H); ESI-MS m/z: 489[M+H]+.

Reference： [1]Altucci, Lucia; Baldari, Cosima T.; Benedetti, Rosaria; Brogi, Simone; Butini, Stefania; Campiani, Giuseppe; Carullo, Gabriele; Federico, Stefano; Fontana, Anna; Gemma, Sandra; Giannaccari, Marialaura; Gorelli, Beatrice; Herp, Daniel; Jung, Manfred; Khan, Tuhina; Lamponi, Stefania; Papa, Alessandro; Passaro, Eugenia; Patrussi, Laura; Pezzotta, Alex; Pistocchi, Anna; Pozzetti, Luca; Ramunno, Anna; Relitti, Nicola; Ruberti, Giovina; Saccoccia, Fulvio; Saponara, Simona; Saraswati, Akella Prasanth; Sarno, Federica; Tatangelo, Vanessa; Valoti, Massimo; Varani, Katia; Vincenzi, Fabrizio [European Journal of Medicinal Chemistry, 2022, vol. 238]
[2]Altucci, Lucia; Baldari, Cosima T.; Benedetti, Rosaria; Brogi, Simone; Butini, Stefania; Campiani, Giuseppe; Carullo, Gabriele; Federico, Stefano; Fontana, Anna; Gemma, Sandra; Giannaccari, Marialaura; Gorelli, Beatrice; Herp, Daniel; Jung, Manfred; Khan, Tuhina; Lamponi, Stefania; Papa, Alessandro; Passaro, Eugenia; Patrussi, Laura; Pezzotta, Alex; Pistocchi, Anna; Pozzetti, Luca; Ramunno, Anna; Relitti, Nicola; Ruberti, Giovina; Saccoccia, Fulvio; Saponara, Simona; Saraswati, Akella Prasanth; Sarno, Federica; Tatangelo, Vanessa; Valoti, Massimo; Varani, Katia; Vincenzi, Fabrizio [European Journal of Medicinal Chemistry, 2022, vol. 238]

88
[ 117-34-0 ]
[ 7732-18-5 ]
[ 1067-55-6 ]
[diphenylacetate]₄[Bu₂Sn]₄(μ₃-O)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	In methanol at 20℃; for 3h;

Reference： [1]Diasse-Sarr, Aminata; Diop, Cheikh Abdoul Khadir; Diop, Mouhamadou Birame; Diop, Tidiane; Dumitru, Florina; Sidibe, Mamadou; Van Der Lee, Arie [Main Group Metal Chemistry, 2022, vol. 45, # 1, p. 35 - 43]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	117-34-0	MDL No. :	MFCD00004251
Formula :	C₁₄H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PYHXGXCGESYPCW-UHFFFAOYSA-N
M.W :	212.24	Pubchem ID :	8333
Synonyms :		Chemical Name :	2,2-Diphenylacetic acid

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.47
TPSA :	37.3 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.4 cm/s

Log Po/w (iLOGP) :	1.52
Log Po/w (XLOGP3) :	3.09
Log Po/w (WLOGP) :	2.9
Log Po/w (MLOGP) :	3.15
Log Po/w (SILICOS-IT) :	2.97
Consensus Log Po/w :	2.72

[ CAS No. 117-34-0 ] {[proInfo.proName]}

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[ 117-34-0 ] Synthesis Path-Upstream 1~3

[ 117-34-0 ] Synthesis Path-Downstream 1~88

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[ 117-34-0 ]

Aryls

Carboxylic Acids

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Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Log S (ESOL) :	-3.46
Solubility :	0.0737 mg/ml ; 0.000347 mol/l
Class :	Soluble
Log S (Ali) :	-3.54
Solubility :	0.0611 mg/ml ; 0.000288 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.34
Solubility :	0.00963 mg/ml ; 0.0000454 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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P103	Read label before use
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P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 117-34-0 ] {[proInfo.proName]}

Quality Control of [ 117-34-0 ]

Related Doc. of [ 117-34-0 ]

Product Details of [ 117-34-0 ]

Calculated chemistry of [ 117-34-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 117-34-0 ]

Application In Synthesis of [ 117-34-0 ]

[ 117-34-0 ] Synthesis Path-Upstream 1~3

[ 117-34-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 117-34-0 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 117-34-0 ]