Name: 1123-00-8|2-Cyclopentylacetic acid|98%
Brand: Ambeed
SKU: A104161
Price: 11.0 USD
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1
[ 1123-00-8 ]
[ 1122-99-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In N,N-dimethyl-formamide;	EXAMPLE 176 Preparation of cyclopentylacetyl chloride To a solution of 50 g. of <strong>[1123-00-8]cyclopentaneacetic acid</strong> containing 2.9 ml. of N,N-dimethylformamide is added dropwise, with stirring, 51 g. of thionyl chloride over a period of 15 minutes. After stirring for an additional 60 minutes excess thionyl chloride is removed in vacuo and the residual oil is distilled to give 55.4 g. (97%) of product, b.p. 57-58 C. (10 mm.).
	With Chloro-oxo-acetic acid;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	To a solution of <strong>[1123-00-8]cyclopentylacetic acid</strong> (4.94 g, 38.51 mmol) and DMF (one drop) in DCM (100 mL), oxalylchloride (23.1 mL, 2.0 M in DCM, 1.2 eq, 46.2 mmol) was added dropwise over one hour at room temperature. The reaction was stirred for another two hours, evaporated under reduced pressure and dried under vacuum to afford crude cyclopentylacetyl chloride. This residue was dissolved in THF (80 mL) and cooled to -78 C. To a solution of 4S-benzyloxazolidinone (6.79 g, 38.5 mmol) in THF (50 mL) at -78 C., nBuLi (26.2 mL, 1.45 M, 38 mmol) was added dropwise by syringe and stirred for an additional 15 minutes producing lithiated oxazolidinone. This solution was added over 30 minutes via cannula to the solution of cyclopentylacetyl chloride. The reaction mixture was stirred 30 minutes at -78 C. before quenching with 1 M NaH2SO4 (75 mL). The THF was removed under reduced pressure and the aqueous layer was extracted with DCM (3×75 mL). The combined organics were washed with 10% NaHCO3 aq. (50 mL), brine (50 mL), dried over Na2SO4, filtered and evaporated onto silica (15 g). The product was purified by chromatography (silica gel, 5-20% EtOAc in hexanes) to give 7.97 g (70%) of a white solid: [alpha]20D=+52.00 (c 1, CHCL3); IR (film) 2948, 2835, 1779, 1696, 1455, 1383, 1352, 1210, 1099, 700 cm-1; 1H NMR (400 MHz, CDCL3) delta 7.2-7.4 (m, 5H), 4.67 (m, 1H), 4.16, (M, 2H), 3.30 (dd, J=3.3, 13.3, 1H), 3.02 (dd, J=6.9, 16.6, 1H), 2.90 (dd, J=7.4, 16.6, 1H), 2.77 (dd, J=9.7, 13.3, 1H), 2.33 (m, 1H), 1.89 (m. 2H), 1.62 (m, 4H), 1.22 (m, 2H); 13C NMR (100 MHz, CDCL3) delta 172.9, 153.4, 135.3, 127.2, 66.0, 55.1, 41.3, 37.9, 35.7, 32.44, 32.38, 24.9; HRMS (CI+, NH3) calc'd for C17H21NO3: 305.1865, found 305.1870.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 12h;Inert atmosphere;	General procedure: Cyclopropyl acetic acid (1.00 g, 9.98 mmol) was taken in 35.0 mL of dry CH2Cl2 at 0 C and catalytic amount of DMF (1 drop) was added. The solution was stirred and treated with oxalyl chloride (0.9 mL, 10.40 mmol) dropwise. The resulting mixture was stirred overnight slowly warming to room temperature. After 12 hours, the solvent was evaporated in rotavapor minimizing exposure to air to yield the crude acid chloride. The crude product thus obtained was immediately used for the next step without further purification. A solution of (R)-4-benzyloxazolidin-2-one (1.32 g, 7.50 mmol) in 30.0 mL of dry THF was cooled to -78 oC under argon atmosphere, and treated with dropwise addition of n-BuLi (4.46 mL, 1.68 M in Hexanes, 7.50 mmol). The resulting mixture was stirred for 20 minutes at the same temperature, and a solution of acid chloride (obtained above) in 45.0 mL of dry THF was slowly added via cannula. The reaction was stirred at -78 oC for 30 minutes and at 0 oC for 1.5 hours. TLC examination revealed complete conversion of the starting material. The mixture was then quenched with saturated solution of NH4Cl and extracted with EtOAc (2 x 20 mL). The aqueous layer was further extracted with EtOAc and the combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography using hexanes-EtOAc: 8:2 to afford the title compound. Physical and spectral properties of compounds 6a [3] and 6e [4] are in agreement with the literature.

	With thionyl chloride; In N,N-dimethyl-formamide;	EXAMPLE 114 Preparation of cyclopentylacetyl chloride To a solution of 50 g. of <strong>[1123-00-8]cyclopentaneacetic acid</strong> containing 2.9 ml. of N,N-dimethylformamide is added dropwise with stirring, 51 g. of thionyl chloride over a period of 15 minutes. After stirring for an additional 60 minutes excess thionyl chloride is removed in vacuo and the residual oil is distilled to give 55.4 g. (97%) of product, b.p. 57-58 C. (10 mm.).
	With thionyl chloride; In N,N-dimethyl-formamide;	EXAMPLE 31 Preparation of cyclopentylacetyl chloride To a solution of 50 g. of <strong>[1123-00-8]cyclopentaneacetic acid</strong> containing 2.9 ml. of N,N-dimethylformamide is added dropwise with stirring, 51 g. of thionyl chloride over a period of 15 minutes. After stirring for an additional 60 minutes exces thionyl chloride is removed in vacuo and the residual oil is distilled to give 55.4 g. (97%) of product, b.p. 57-58 C. (10 mm.).
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 4h;	Oxalyl chloride (0.178ml, 2mmol) in DCM (1 ml) was added to a stirred solution of <strong>[1123-00-8]cyclopentylacetic acid</strong> (0.19g, 1.48mmol) in DCM (10ml). A 1 : 1 mixture of DMF/DCM (1 drop) was added and the reaction mixture stirred at room temperature for 4h. One tenth of this solution was then added to a solution of 3-fluoro-4-(4-morpholinyl)-N-[(1-[4-(trifluoromethyl)phenyl]methyl}-4-piperidinyl)methyl]aniline D10 (0.09g, 0.2mmol) and triethylamine (0.06g, 0.6mmol) in DCM (2ml) and the mixture shaken for 24h. The mixture was washed with saturated sodium hydrogen carbonate and the organic layer separated by passage through a phase separation cartridge and evaporated in vacuo. The residue was dissolved in 1 : 1 DMSO/MeCN (0.5ml) and purified by mass directed autoprep hplc on a Waters C18 5muM column 8(id 19 x 100mm) eluting with 5 - 99% MeCN in water gradient containing 0.1 % formic acid to afford the title compound as a colourless gum (0.05g, 60%). Mass Spectrum (AP+): Found 562 (MH+). C31H39F4N3O2 requires 561.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃;	2-cyclopentylacetamide; To a solution of <strong>[1123-00-8]cyclopentylacetic acid</strong> (1) (5.0 g, 39.01 mmol) in dichloromethane 50 mL at 0 0C was added oxalyl chloride (5.94 g, 46.81 mmol) dropwise, followed by a drop of DMF. Reaction was allowed to stir overnight at room temperature. Solvent was evaporated to provide a crude oil, which was dissolved in acetonitrile 30 ml. Then the crude acid chloride 2 was slowly added to a cooled soluton of 30 % ammonium hydroxide. Then the reaction was allowed to stir at room temperature. After the reaction was complete (30 min) solvent was evapoarted. The product <n="80"/>crystallized out, was filtered off, and washed with water and ether to provide a white solid 3 (2.70 g, 54.4 %). 1H NMR (400 MHz, DMSO-ct°) 1.09 (m, 2H), 1.44-1.74 (m, 6H), 2.03 (m, 2H), 2.11 (m, IH), 6.67 (bs, IH), 7.21 (bs, IH). M+ 128.2.

Reference： [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 764 - 771
[2]Patent: US2444024,1946,
[3]Journal of the American Chemical Society,1981,vol. 103,p. 7232 - 7234
[4]Chemical and Pharmaceutical Bulletin,1987,vol. 35,p. 2426 - 2436
[5]Journal of the American Chemical Society,1986,vol. 108,p. 7686
[6]Journal of the American Chemical Society,1997,vol. 119,p. 1805 - 1806
[7]Journal of Medicinal Chemistry,2006,vol. 49,p. 3332 - 3344
[8]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3449 - 3453
[9]Journal of Pharmacology and Experimental Therapeutics,2006,vol. 318,p. 173 - 185
[10]Patent: US4236027,1980,A
[11]Patent: US6982082,2006,B1 .Location in patent: Page/Page column 36-37
[12]Journal of Medicinal Chemistry,2013,vol. 56,p. 437 - 450
[13]Journal of Medicinal Chemistry,2014,vol. 57,p. 4154 - 4172
[14]Journal of the American Chemical Society,2014,vol. 136,p. 17662 - 17668
[15]European Journal of Medicinal Chemistry,2018,vol. 157,p. 962 - 977
[16]Patent: US4076947,1978,A
[17]Patent: US4180677,1979,A
[18]Patent: WO2005/103000,2005,A1 .Location in patent: Page/Page column 40-41
[19]Patent: WO2009/114950,2009,A1 .Location in patent: Page/Page column 78-79
[20]Organic Letters,2019
[21]Organic Letters,2019,vol. 21,p. 2808 - 2812
[22]Organic Letters,2020,vol. 22,p. 997 - 1002

2
[ 1123-00-8 ]
[ 6053-81-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen azide; chloroform

Reference： [1]v. Braun; Anton [Chemische Berichte, 1933, vol. 66, p. 1373,1375] Ney et al. [Journal of the American Chemical Society, 1943, vol. 65, p. 770,775]

3
[ 1123-00-8 ]
[ 53389-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus; bromine

Reference： [1]Current Patent Assignee: SANOFI - DE965324, 1955, C

4
[ 13668-61-6 ]
[ 1123-00-8 ]

Reference： [1]Angewandte Chemie,1981,vol. 93,p. 107
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1938,vol. 256,p. 85,89
[3]Chemisches Zentralblatt,1909,vol. 80,p. 2146

5
[ 1123-00-8 ]
[ 933-04-0 ]

Yield	Reaction Conditions	Operation in experiment
98%		A flame-dried flask with stir bar was charged with <strong>[1123-00-8]cyclopentylacetic acid</strong> (2.56 g, 20.0 mmol, 1.0 equiv) and fitted with a rubber septum. The flask was evacuated and backfilled with N2. ACS grade CH2Cl2 (66 mL, 0.3 M) was added via syringe. Carbonyl diimidazole (CDI, 4.06 g, 25.0 mmol, 1.25 equiv) was then added by briefly removing the septum and adding the solid as asingle portion. The reaction was left to stir at 22 C for 1 h. After 1 h, the reaction flask wascooled at 0 C in an ice water bath and aqueous NH4OH (30%) (9.4 mL, 72.4 mmol, 3.6 equiv)) was added. Following NH4OH addition, the reaction was allowed to slowly warm to room temperature by not removing the ice bath and stirred overnight. After stirring overnight, the biphasic suspension was transferred to a separatory funnel anddiluted with saturated aqueous NaHCO3 (ca. amount of CH2Cl2). The reaction flask was rinsed with an additional 5 mL CH2Cl2 to ensure quantitative transfer. The organic phase was removedand the aqueous was extracted once more with CH2Cl2. The combined organic phases were washed with 1 M HCl, dried over Na2SO4, filtered, and concentrated under reduced pressure. Typically, the crude material did not require further chromatographic purification. The product was obtained as a white solid (2.49 g, 98% yield) without chromatographic purification. 1H NMR (400 MHz, CDCl3) delta 5.85 (br s, 1H), 5.53 (br s, 1H), 2.24-2.15 (m, 3H), 1.87-1.82 (m,2H), 1.64-1.50 (m, 4H), 1.19-1.11 (m, 2H). 13C NMR (126 MHz, CDCl3) delta 175.7, 42.1, 36.9, 32.5, 24.9. IR (neat) nu 3346 (br m), 3168 (br m), 2951 (m), 2867 (m), 1661 (s), 1629 (s), 1412 (s), 1353 (m), 1308 (m), 1250 (m), 1156 (m), 952 (w), 882 (w), 809 (w), 672 (s) cm-1. TLC Rf = 0.19 in 1:1 CH2Cl2:EtOAc. HRMS (ESI) m/z: [M + H]+ Calcd for C7H13NO 128.1070; Found 128.1068.
52%	With thionyl chloride; In ammonium hydroxide; dichloromethane; N,N-dimethyl-formamide;	A. Cyclopentylacetic acid (5.2 g, 41 mmol) and thionyl chloride (10 mL) were combined then DMF (0.2 mL) was added and the solution was stirred 1.5 h at R.T. Dichloromethane (10 mL) was added and the solution cooled in an ice bath whereupon 25% aqueous ammonia (30 mL) was added and the mixture stirred for 0.5 h. The solution was extracted with CH2 Cl2 (3*) and the combined extracts washed with 1N HCl, dried over MgSO4, and concentrated to give cyclopentylacetamide (2.699 g, 52%). ?1[H]-NMR(CDCl3) consistent with structure.
	With ammonia; at 165℃; for 0.5h;	General procedure: Into a 1L open reactor was added 500g of carboxylic acid feedstock (chemically pure), stirring was turned on (600 r/min), ammonia gas was continuously fed to the carboxylic acid feed from the bottom of the reactor (chemical purity, water content was 5.1wt%, Flow rate is 100g/min). After the reaction was allowed to proceed for TC hours at the reaction temperature TA, the ammonia gas flow was stopped. The contents of the reactor were sampled and nuclear magnetic proton spectra and elemental analysis were performed to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the obtained amide intermediate has an extremely high purity (above 99%).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wt% of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min).

To a solution of [1123-00-8]2-[1123-00-8]cyclopentylacetic acid (500 mg, 3.90 mmol) in toluene (10 mL) was added sulfurous dichloride (4641 mg, 39.0 mmol) , the mixture was heated to reflux for 2 h. The reaction mixture was concentrated in vacuum the residue was dissolved in THF (10 mL) and sat. solution of ammonia in THF (0.2 mL) was added, the mixture was stirred at room temperature overnight. Filtered and the filtration was concentrated to give the title compound.1H NMR (DMSO-d6, 400 MHz) : delta 7.18 (bs, 1H) , 6.64 (bs, 1H) , 1.93-2.13 (m, 3H) , 1.66 (d, J 5.9 Hz, 2H) , 1.39-1.58 (m, 4H) , 1.07 (m, 2H) .

Reference： [1]Tetrahedron,2019,vol. 75,p. 3186 - 3194
[2]Patent: US5723490,1998,A
[3]Journal of the American Chemical Society,1965,vol. 87,p. 1600 - 1607
[4]Patent: CN104557610,2018,B .Location in patent: Paragraph 0138; 0139; 0140; 0149; 0150
[5]Patent: WO2019/238,2019,A1 .Location in patent: Page/Page column 72
[6]Organic Letters,2019
[7]Organic Letters,2020,vol. 22,p. 997 - 1002

6
[ 1123-00-8 ]
[ 766-00-7 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of lithium aluminium hydride (8.3 g, 218.4 mmol) in dry tetrahydrofuran (300 mL) at 0 C. was added a solution of <strong>[1123-00-8]cyclopentylacetic acid</strong> (20 g, 156 mmol) in tetrahydrofuran (15 mL) dropwise. The mixture was then heated at 80 C. for 14 h. The reaction was quenched with a 10% sodium hydroxide solution. The solid formed was filtered off and washed with tetrahydrofuran (3×100 mL). The combined filtrate was dried over anhydrous sodium sulfate, concentrated in vacuo to give 2-cyclopentyl-ethanol as a colorless oil (15.7 g, 80%) which was used without further purification.

Reference： [1]Patent: WO2016/202253,2016,A1 .Location in patent: Page/Page column 368
[2]Journal of the American Chemical Society,2000,vol. 122,p. 8204 - 8214
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 939 - 946
[4]Tetrahedron,1965,vol. 21,p. 2779 - 2789
[5]Tetrahedron,1965,vol. 21,p. 539 - 545
[6]Journal of the American Chemical Society,1965,vol. 87,p. 1288 - 1297
[7]Journal of Medicinal Chemistry,1981,vol. 24,p. 404 - 408
[8]Journal of the American Chemical Society,1984,vol. 106,p. 5295 - 5303
[9]Patent: US2011/144105,2011,A1 .Location in patent: Page/Page column 13

7
[ 67-56-1 ]
[ 1123-00-8 ]
[ 37172-84-2 ]

Yield	Reaction Conditions	Operation in experiment
45%		A DCM (10 mL) solution of <strong>[1123-00-8]2-<strong>[1123-00-8]cyclopentylacetic acid</strong></strong> (5.0 g, 39.0 mmol) under N2 was treated DMF (1 drop) and (COCl)2 ( 2 M in DCM, 19.5 mL, 39 mmmol) at rt. The reaction was stirred for 2 h and then diluted with DCM (20 mL) and treated with NBS (8.3 g, 46.8 mmol) followed by HBr (~ 5.7 M in AcOH, 3 drops) at rt. The reaction was heated at reflux overnight then concentrated under reduced pressure. 1 ,2-Dichloroethane (30 mL) was added followed by NBS (3.4 g, 19.2 mmOL) and HBr (~ 5.7 M in AcOH, 5 drops). The reaction mixture was heated at 80 C for 2.5 h and then cooled to rt. A white precipitate was remove by filtration. The filtrate-90-4820V.1 was collected into a flask containg cold (0C) MeOH (65 niL) and stirred for 30 min before it was concentrated under reduced pressure. The residue was taken into three portions of Et20 decanting the liquid each time. The Et20 solutions were combined , washed (H20 2x), dried (Na2S04) and concentrated under reduced pressure. Purification by flash chromatography (100 Si02 Biotage, 0 -10 % EtOAc in hexanes) afforded methyl 2-bromo-2-cyclopentylacetate as vary pale yellow-orange oil (1.62 g, 45 %).

Reference： [1]Patent: WO2011/123937,2011,A1 .Location in patent: Page/Page column 90-91
[2]Journal of the Chemical Society. Perkin transactions I,1986,p. 1939 - 1946

8
[ 64-18-6 ]
[ 1528-30-9 ]
[ 1123-00-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 3595 - 3596

9
[ 1123-00-8 ]
[ 107754-14-3 ]
[ 107786-49-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃; for 16h;	Carboxylic acid (1 eq.),DMAP (1.5 eq.), EDC (1.2 eq.), and amine (1.2 eq.) were added to DCM (10 mL/mmol of carboxylic acid) in that order. The reactionwas stirred at room temperature for 16 h 2M HCl was added to thereaction. Organic layer was extracted 3 EtOAc. Combined organiclayers were washed with brine. Organic layer was dried withMg2SO4 and rotovapped. Product was purified by column chromatographyPinksolid; 60%; 1H NMR (DMSO): delta 9.61 (s, 1H),7.78-7.72 (m, 1H), 7.52-7.42 (m, 2H), 7.33-7.22 (m, 2H), 7.13 (d,J 7.8 Hz, 1H), 7.06 (s, 1H), 3.98 (s, 2H), 3.93 (s, 3H), 3.83 (s, 3H),3.70 (s, 3H), 2.19e2.03 (m, 1H), 1.81-1.68 (m, 3H), 1.68-1.42 (m,4H), 1.26-1.04 (m, 3H); 13C NMR (DMSO): delta 174.50, 170.64, 166.64,157.20, 135.72, 134.00, 131.76, 129.93, 129.04, 128.97, 127.57, 121.90,115.43, 111.54, 110.93, 109.82, 109.70, 55.99, 52.51, 43.00, 37.23,36.47, 32.78, 32.40, 25.15, 24.99.

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 1781 - 1790
[2]European Journal of Medicinal Chemistry,2018,vol. 157,p. 1202 - 1213

10
[ 1123-00-8 ]
[ 145866-23-5 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 705 - 708

11
[ 1123-00-8 ]
[ 100-51-6 ]
[ 164472-98-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With toluene-4-sulfonic acid; In benzene; for 2h;Reflux;	A mixture of <strong>[1123-00-8]cyclopentylacetic acid</strong> (compound 10, 10.02 g, 78.2 mmol), benzyl alcohol (8.45 g, 78.2 mmol) and p-toluenesulfonic acid monohydrate (1.48 g, 7.82 mmol) in benzene (60 mL) was refluxed under Dean-Stark condition for 2 h, cooled, concentrated under vacuum and redissolved in ether (60 mL). The organic layer was washed successively with water (1 × 25 mL), saturated aq NaHCO3 solution (2 × 25 mL), water (1 × 25 mL), and brine (1 × 25 mL), dried (MgSO4) and evaporated to generate compound 11 (15.40 g, quantitative) as a viscous oil that was utilized in next step without further purification. 1H NMR (300 MHz, CDCl3) delta: 7.35 (m, 5H), 5.10 (s, 2H), 2.40 (d, J = 8 Hz, 2H), 2.26 (m, 1H), 1.81 (m, 2H), 1.6 (m, 4H), 1.18 (m, 2H).
70%	With toluene-4-sulfonic acid; In toluene; for 4h;Dean-Stark; Reflux;	p-Toluene sulfonic acid monohydrate (1.48 g, 7.82 mmol) was added to a solution of <strong>[1123-00-8]cyclopentylacetic acid</strong> (10.0 g, 78.2 mmol) and benzyl alcohol (8.42 g, 78.2 mmol) in toluene (100 ml) at room temperature, a Dean-Stark water separator was mounted, and the mixture was refluxed for 4 hr. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure, the residue was dissolved in ether, the solution was washed with saturated sodium bicarbonate and saturated brine and was dried over anhydrous magnesium sulfate, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate = 97:3) to give the title compound as a light yellow oil (12.0 g, yield 70%). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.38-7.32 (m, 5H), 5.11 (s, 2H), 2.37 (d, J = 7.2 Hz, 2H), 2.31-2.21 (m, 1H), 1.85-1.78 (m, 2H), 1.66-1.50 (m, 4H), 1.20-1.12 (m, 2H).

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 2362 - 2368
[2]Patent: EP2737900,2014,A1 .Location in patent: Paragraph 0089; 0096-0097
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 2276 - 2277

12
[ 1123-00-8 ]
[ 18928-94-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ / tetrahydrofuran / 4 h / Heating 2: pyridine / 18 h 3: NaBr, HMPA / acetone / 6 h / Heating

Reference： [1]Lednicer; Von Voigtlander; Emmert [Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 404 - 408]

13
[ 1123-00-8 ]
[ 18322-54-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1949,p. 475,478

14
[ 1123-00-8 ]
[ 164472-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With p-toluenesulfonic acid monohydrate; benzyl alcohol; In benzene;	Step 1 Preparation of benzyl cyclopentaneacetate: A mixture of <strong>[1123-00-8]cyclopentylacetic acid</strong> (10.02 g, 8.2 mmol), benzyl alcohol (8.45 g, 78.2 mmol) and p-toluenesulfonic acid monohydrate (1.48 g, 7.82 mmol) in benzene (60 mL) was refluxed using a Dean-Stark water separator for 2 h. After cooling, benzene was removed and the mixture was diluted with ether (50 mL) and washed successively with saturated NaHCO3 solution, saturated brine solution, dried and evaporated to give the compound (15.40 g) as an oil; 1 H NMR (300 MHz, CDCl3) delta: 7.35(m, 5H), 5.10(s, 2H), 2.40(d, j=8 Hz, 2H), 2.26(m, 1H), 1.81 (m, 2H), 1.6 (m, 4H), 1.18(m, 2H).
	With p-toluenesulfonic acid monohydrate; benzyl alcohol; In benzene;	Step 1 Preparation of benzyl cyclopentaneacetate: A mixture of <strong>[1123-00-8]cyclopentylacetic acid</strong> (10.02 g, 78.2 mmol), benzyl alcohol (8.45 g, 78.2 mmol) and p-toluenesulfonic acid monohydrate (1.48 g, 7.82 mmol) in benzene (60 mL) was refluxed using a Dean-Stark water separator for 2h. After cooling, benzene was removed and the mixture was diluted with ether (50 mL) and washed successively with saturated NaHCO3 solution, saturated brine solution, dried and evaporated to give the compound (15.40 g) as an oil; 1 H NMR (300 MHz, CDCl3)delta: 7.35(m, 5H), 5.10(s, 2H), 2.40(d, j=8 Hz, 2H), 2.26(m, 1H), 1.81 (m, 2H), 1.6 (m, 4H), 1.18(m, 2H).

Reference： [1]Bulletin de la Societe Chimique de France,1949,p. 475,478
[2]Patent: US5550262,1996,A
[3]Patent: US5614649,1997,A

15
[ 197455-87-1 ]
[ 1123-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bei der Destillation im Vakuum 2: hydrogen; nickel / 170 - 175 °C / Hydrogenation

Reference： [1]Eijkman [Chemisches Zentralblatt, 1909, vol. 80, # II, p. 2146]

16
(S)-5-aminomethyl-3-(1,4,5,6-tetrahydro-1,2-diaza-benzo[e]azulen-8-yl)-oxazolidin-2-onehy drochloride [ No CAS ]
[ 1123-00-8 ]
[ 741722-19-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tert-butyl alcohol; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 24h;	The title compound was prepared using (S)-5-AMINOMETHYL-3- (1, 4,5, 6- TETRAHYDRO-1, 2-diaza-benzo [e] AZULEN-8-YL)-OXAZOLIDIN-2-ONE hydrochloride, 2.2 EQ. t-butanol, 2.2 eq. <strong>[1123-00-8]cyclopentyl acetic acid</strong>, 2.2 eq EDCI and 6 eq. of triethylamine as described in general procedure DD. Yield: 0.175 g (56%). Melting point: 165- 167 C. MS: AP+: 519. 3. General Procedure DD : To a stirring solution of the amine (for example, see Example 73,76, and 78) (200 mg, 0.3 mmol), the corresponding acid (2.2 eq), t- butanol (2.2 eq) and EDCI (2.2 eq. ) in DMF (5 ML) at 0 C under nitrogen was added diisopropylethylamine (6 eq). The mixture was stirred for 24 hours while slowly warming to room temperature. The reaction mixture was then diluted with saturated sodium bicarbonate and brine and extracted with methylene chloride. The combined organic layers were dried, filtered and concentrated in vacuo and the residue purified via flash chromatography to afford the desired amides.

Reference： [1]Patent: WO2004/69832,2004,A2 .Location in patent: Page 176-177

17
(D,L)-alanine iso-butyl ester hydrochloride [ No CAS ]
[ 1123-00-8 ]
N-(cyclopentylacetyl)-L-alanine iso-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example B71 Synthesis of N-(cyclopentylacetyl)-L-alanine Iso-butyl Ester Following General Procedure BB above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example BB above), the title compound was prepared as a solid having a melting point of 62 C.-64 C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl. NMR data was as follows: 1H-nmr (CDCl3): delta=0.87 (d, J=6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J=7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d, J=7.1Hz, 1H). 13C-nrnr (CDCl3): delta=18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49.
		Example B71 Synthesis of N-(Cyclopentylacetyl)-L-alanine iso-Butyl Ester Following General Procedure BB above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example BB above), the title compound was prepared as a solid having a melting point of 62 C.-64 C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl. NMR data was as follows: 1H-nmr (CDCl3): delta=0.87 (d, J=6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J=7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d, J=7.1 Hz, 1H). 13C-nmr (CDCl3): delta=18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49. C14H25NO3 (MW=255.36, Mass Spectroscopy (MH+256)).
		Example 71 Synthesis of N-(cyclopentylacetyl)-L-alanine iso-butyl ester Following General Procedure B above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B above), the title compound was prepared as a solid having a melting point of 62 C.-64 C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2 O followed by washes with aqueous K2 CO3 and aqueous HCl. NMR data was as follows: 1 H-nmr (CDCl3):=0.87 (d, J=6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J=7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d, J=7.1 Hz, 1H). 13 C-nmr (CDCl3): delta=18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49.

		EXAMPLE A71 Synthesis of N-(cyclopentylacetyl)-L-alanine iso-butyl ester Following General Procedure B' above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B' above), the title compound was prepared as a solid having a melting point of 62 C.-64 C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl. NMR data was as follows: 1H-nmr (CDCl3): delta=0.87 (d, J=6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J=7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d, J=7.1 Hz, 1H). 13C-nmr (CDCl3): delta=18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49.
		EXAMPLE A71 Synthesis of N-(cyclopentylacetyl)-L-alanine Iso-butyl Ester Following General Procedure B' above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B' above), the title compound was prepared as a solid having a melting point of 62 C.-64 C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl. NMR data was as follows: 1H-nmr (CDCl3): delta=0.87 (d, J=6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J=7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d, J=7.1 Hz, 1H). 13C-nmr (CDCl3): delta=18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49.
		Example A71 Synthesis of N-(cyclopentylacetyl)-L-alanine iso-butyl ester Following General Procedure B' above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B' above), the title compound was prepared as a solid having a melting point of 62 C.-64 C. The reaction was monitored by tlc on silica gel (Rf=0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl. NMR data was as follows: 1H-nmr (CDCl3): delta=0.87 (d, J=6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J=7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d,J=7.1 Hz, 1H). 13C-nmr (CDCl3): delta=18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49.
	With 1,1'-carbonyldiimidazole; triethylamine; In tetrahydrofuran;	Example 71 Synthesis of N-(cyclopentylacetyl)-L-alanine iso-butyl ester Following General Procedure B above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and L-alanine iso-butyl ester hydrochloride (from Example B above), the title compound was prepared as a solid having a melting point of 62C-64C. The reaction was monitored by tlc on silica gel (Rf = 0.37 in 1:3 EtOAc:hexane) and purification was by extraction with Et2O followed by washes with aqueous K2CO3 and aqueous HCl. NMR data was as follows: 1H-nmr (CDCl3): delta = 0.87 (d, J = 6.8 Hz, 6H), 1.01-1.17 (m, 2H), 1.34 (d, J = 7.2 Hz, 3H), 1.40-1.62 (m, 4H), 1.70-1.83 (m, 2H), 1.89 (m, 1H), 2.15 (m, 3H), 3.86 (m, 2H), 4.55 (m, 1H), 6.30 (d, J = 7.1 Hz, 1H). 13C-nmr (CDCl3): delta = 18.4, 18.78, 18.80, 24.8 (very high), 27.5, 32.27, 32.32, 36.9, 42.5, 47.7, 71.2, 172.2, 173.2. Elemental Analysis-Calc (%): C, 65.85; H, 9.87; N, 5.49; Found (%): C, 66.01; H, 10.08; N, 5.49. C14H25NO3 (MW = 255.36, Mass Spectroscopy (MH+ 256)). GENERAL PROCEDURE BCoupling of R1C(X')(X")C(O)OH with H2NCH(R2)C(O)XR3 A solution of the acid (3.3 mmol) and CDI in 20 mL THF was stirred for 2 h. L-alanine iso-butyl ester hydrochloride (from Example B below) (3.6 mmol) was added, followed by 1.5 mL (10.8 mmol) of triethylamine. The reaction mixture was stirred overnight. The reaction mixture was diluted with 100 mL of diethyl ether, washed with 10% HCl three times, brine once, 20% potassium carbonate once and brine once. The solution was dried over magnesium sulfate, filtered, and evaporated at reduced pressure to yield the product. Other amino acid esters may also be employed in this procedure

Reference： [1]Patent: US2002/45747,2002,A1
[2]Patent: US6506782,2003,B1
[3]Patent: US6117901,2000,A
[4]Patent: US6191166,2001,B1
[5]Patent: US6207710,2001,B1
[6]Patent: US6211235,2001,B1
[7]Patent: EP951464,2005,B1 .Location in patent: Page/Page column 47; 27

18
[ 859285-26-0 ]
[ 1123-00-8 ]
C₂₃H₃₁ClN₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 24h;	A mixture of the appropriate acid, ZCO2H, (1.2 eq.), 1-hydroxybenzotriazole hydrate (1.2 eq.), triethylamine (2 to 4 eq.) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.2 eq.) and the appropriate amine, or amine hydrochloride, selected from preparations 2 and 143 (1 eq.) in dichloromethane (26 mlmmol-1) was stirred at room temperature for 24 hours. The reaction was then washed with 2N sodium hydroxide solution and the organic solution was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:methanol:0.88 ammonia (100:0:0 to 95:5:0.5) to afford the title compounds.

Reference： [1]Patent: US2005/154024,2005,A1 .Location in patent: Page/Page column 60-61

19
(1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]propan-1-ol [ No CAS ]
[ 1123-00-8 ]
2-cyclopentyl-N-[(1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-[4-(trifluoromethyl)benzyl]ethyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20℃;	While stirring (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]propan-1-ol (0.156 g, 0.498 mmol), <strong>[1123-00-8]cyclopentylacetic acid</strong> (64 mg, 0.50 mmol) and 1-hydroxybenzotriazole hydrate (76 mg, 0.50 mmol) in acetonitrile (10 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (95 mg, 0.50 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and passed through silica gel. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from hexane to give the objective substance. white crystal yield 0.185 g, 88% mp 195-196C; 1H-NMR (CDCl3-DMSO-d6, 200MHz) delta 0.75-1.05 (2H, m), 1.25-1.65 (6H, m), 1.92 2.12 (3H, m), 2.77-2.81 (2H, m), 4.39-4.52 (1H, m), 4.65 (1H, d, J = 3.4 Hz), 4.93 (1H, t, J = 3.3 Hz), 6.10 (1H, br d, J = 8.4 Hz), 7.06 (2H, t, J! = 8.8 Hz), 7.21 (2H, d, J = 8.0 Hz), 7.39-7.49 (4H, m); IR (KBr) 3301, 2949, 1645, 1539, 1514, 1327, 1163, 1125, 1069, 829 cm-1; Anal. Calcd for C23H25F4NO2: C, 65.24; H, 5.95; N, 3.31. Found: C, 65.08; H, 5.90; N, 3.41.

Reference： [1]Patent: EP1362846,2003,A1 .Location in patent: Page/Page column 56

20
[ 67-56-1 ]
[ 1123-00-8 ]
[ 2723-38-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With chloro-trimethyl-silane; at 20℃;	5.15 g (39 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong>, 2.45 ml (59 mmol) of methanol and 2.52 ml (20 mmol) of trimethylsilyl chloride are introduced into a 50 ml pear-shaped flask. The reaction mixture is stirred at room temperature overnight. Two phases are formed. NaHCOs is added to alkaline pH, the mixture is extracted with CH2CI2, washed with H2O, dried and evaporated (50C/80 mm Hg): 5.5 g (99%) of ester 300DN41 IV are obtained in the form of an oil. 1H NMR: (CDC.3): 1.02-1.29 (2H, m); 1.43-1.99 (6H, m); 2.09-2.46 (3H, m); 3.64 (3H, s).

Reference： [1]Patent: WO2006/10423,2006,A2 .Location in patent: Page/Page column 78
[2]ChemMedChem,2017,vol. 12,p. 1693 - 1696

21
[ 1029971-74-1 ]
[ 1123-00-8 ]
[ 1029970-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In ISOPROPYLAMIDE; at 20℃;	Example 61 (IZ)-I -(3-butyl-5-methyl-l,3,4-thiadiazol-2(3H)-ylidene)-3-cyclopentylacetoneIn a 20 mL vial <strong>[1123-00-8]2-<strong>[1123-00-8]cyclopentylacetic acid</strong></strong> (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (77 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (53 mg in 0.7 mL of DMA, 0.4 mmol, 2.40 equiv.), and finally 3-butyl-2,5-dimethyl-l,3,4-thiadiazol-3-ium iodide (50 mg in 0.7 mL of DMA, <n="90"/>U.17 mmol, 1 equiv.). l he mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1 : 1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) delta ppm theta.89 (t, 3 H) 1.06 - 1.16 (m, 2 H) 1.24 - 1.34 (m, 2 H) 1.43 - 1.54 (m, 2 H) 1.53 - 1.61 (m, 2 H) 1.63 - 1.73 (m, 4 H) 2.14 - 2.23 (m, 1 H) 2.30 - 2.34 (m, 2 H) 2.39 - 2.43 (m, 3 H) 4.03 (t, 2 H) 5.90 (s, 1 H); MS (ESI) m/z 281 (M+H)+.

Reference： [1]Patent: WO2008/63781,2008,A2 .Location in patent: Page/Page column 88-89

22
[ 1123-00-8 ]
[ 15028-40-7 ]
[ 208117-04-8 ]

Yield	Reaction Conditions	Operation in experiment
		GENERAL PROCEDURE A First EDC Coupling Procedure To a 1:1 mixture of the corresponding carboxylic acid and the corresponding amino acid ester or amide in CH2Cl2 at OC was added 1.5 equivalents triethylamine, followed by 2.0 equivalents hydroxybenzotriazole monohydrate and then 1.25 equivalents of ethyl-3-(3-dimethylamino)propyl carbodiimide HCl. The reaction mixture was stirred overnight at room temperature and then transferred to a separatory funnel. The mixture was washed with water, saturated aqueous NaHCO3, 1N HCl and saturated aqueous NaCl, and then dried over MgSO4. The resulting solution was stripped free of solvent on a rotary evaporator to yield the crude product.; Step A - Preparation of N-(Cyclopentylacetyl)-L-phenylglycine Methyl Ester Following General Procedure A above using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) and phenylglycine methyl ester hydrochloride (Novabiochem), the title compound was prepared as a solid having a melting point of 83-86C. The reaction was monitored by tlc on silica gel (Rf = 0.28 in 25% ethyl acetate/hexanes) and purification was by recrystallization from ethyl acetate/hexanes. NMR data was as follows: 1H-nmr (CDCl3): delta = 7.35 (s, 5H), 6.44 (bd, 1H), 5.6 (d, 1H), 3.72 (s, 3H), 2.24 (bs, 3H), 1.9-1.4 (m, 6H), 1.2-1.05 (m, 2H). 13C-nmr (CDCl3): delta = 172.3, 171.7, 136.7, 129.0, 128.6, 127.3, 56.2, 52.7, 42.5, 36.9, 32.40, 32.38, 24.8. C16H21NO3 (MW = 275.35); mass spectroscopy (M+Na) 298.; Example B77 Synthesis of N-(cyclopentylacetyl)-L-phenylglycine methyl ester Following General Procedure BD above, and using <strong>[1123-00-8]cyclopentylacetic acid</strong> (Aldrich) with L-phenylglycine methyl ester hydrochloride (Bachem) the title compound was prepared. NMR data was as follows: 1H-nmr (CDCl3): delta = 7.35 (s, 5H), 6.44 (bd, 1H), 5.6 (d, 1H), 3.72 (s, 3H), 2.24 (bs, 3H), 1.9-1.4 (m, 6H), 1.2-1.05 (m, 2H) 13C-nmr (CDCl3): delta = 172.3, 171.7, 136.7, 129.0, 128.6, 127.3, 56.2, 52.7, 42.5, 36.9, 32.40, 32.38, 24.8

Reference： [1]Patent: EP951466,2009,B1 .Location in patent: Page/Page column 61; 64-65; 304

23
[ 1123-00-8 ]
[ 112275-50-0 ]
[ 1148033-41-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step 3: Synthesis of 4-(2-Cyclopentyl-acetyl)-perhydro-l,4-diazepine-l-carboxylic acid terf-butyl ester; To a solution of 2.2 mL (17.7 mmol) of <strong>[1123-00-8]cyclopentyl-acetic acid</strong> and 2.03 g (21.1 mmol) of 1- hydroxybenzotriazole in 20 mL dimethylformamide is added 4.05 g (21.1 mmol) of N-(3- dimethylaminopropyl)-N'-ethylcarbodiimide. After 15 min of stirring at room temperature 3 mL (15.4 mmol) of te/t-butyl-l-homopiperazinecarboxylate is added, then 75 mg (0.62 mmol) <n="30"/>of dimethylaminopyridine is added. The reaction mixture is left stirring for 18 hours at room temperature. Water is added and it is extracted with ethyl acetate twice. The organics are combined and washed with water, saturated sodium bicarbonate aqueous solution, saturated, ammonium chloride aqueous solution and brine, dried (Na2SO4), filtered and concentrated. The residue is purified by flash chromatography using 50 % ethyl acetate/hexanes then switched to 5 % methanol/dichloromethane as eluent mixtures. 4.05 g slightly yellow oil is obtained as the product.

Reference： [1]Patent: WO2009/55357,2009,A1 .Location in patent: Page/Page column 26; 28-29

24
[ 1123-00-8 ]
[ 5351-69-9 ]
5-cyclopentylmethyl-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%		A solution of CYCLOPENTYLACETIC acid (0.26 g, 2.0 mmol) in SOC12 (0.4 ML) was stirred at ambient temperature for 1 h. The excess of SOC12 was evaporated in vacuo. The residue was dissolved in chloroform (5 mL). 4-Phenyl-3-thiosemicarbazide (0.32 g, 1.9 mmol) and pyridine (0.1 ML) were added and the resulting solution was stirred for 1.5 h. The solvent was evaporated in vacuo and the resulting oil was dissolved in MEOH (1 mL) and 1% NAOH (5 mL) was added. The reaction mixture was stirred at ambient temperature overnight and then at 50 C for 2 h. The reaction mixture was diluted with water and neutralized with 2M hydrochloric acid. The resulting precipitate was collected by filtration and washed with water giving 0.16 g (31%) of the title compound. H NMR (DMSO-D6) 8 13.7 (1H, s), 7.54 (3H, m), 7.39 (2H, M), 2.40 (2H, d, J=7.0 Hz), 1.95 (1H, d, J=7.0 Hz), 1.63 (2H, m), 1.52-1. 37 (4H, m), 1.04 (2H, m); L3C NMR (DMSO-d6) 8 167.5, 151.8, 133.8, 129.4, 128.3, 36.3, 31.7, 31.1, 24.4 ; MS (ESI) m/z 260 (M+1).

Reference： [1]Patent: WO2004/96781,2004,A1 .Location in patent: Page 68-69

25
[ 64-17-5 ]
[ 1123-00-8 ]
[ 18322-54-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; for 3h;Reflux;	Concentrated sulfuric acid (1 mL) was added to a solution of cyclopentylacetic acid (5.8 mL, 46 mmol) in anhydrous EtOH (15 mL) and heated to reflux for 3 hours. Thereafter, volatiles were removed under reduced pressure and the residue was diluted with water and ethyl acetate. The organic layer was separated, washed with 5% sodium bicarbonate, brine, dried over Na2SO4, and filtered. After evaporation of solvent under reduced pressure, a syrupy cyclopentylacetic acid ethyl ester was obtained and used in the next step without further purification.

Reference： [1]Patent: US2010/144731,2010,A1 .Location in patent: Page/Page column 19

26
[ 1123-00-8 ]
[ 1242435-93-3 ]
[ 1242435-46-6 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of example compound 14: 2-Cyclopentyl-N-[2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide254 mul (3.0 mmol) oxalylchloride were added to a solution of 192 mg (1.5 mmol) 2-<strong>[1123-00-8]cyclopentyl acetic acid</strong> in DCM (10 ml) and the mixture was stirred for 3 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with dioxane (6 ml). This solution was added at 0 C. to a solution of 362 mg (1.0 mmol) [2-[2-[[3-(trifluoromethyl)phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]amine (VPF-001) in dioxane (5 ml). Then the reaction solution was mixed with 420 mg (5.0 mmol) NaHCO3 and stirred for 16 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with water. Then it was extracted with EE and the organic phase was washed with a saturated aqueous NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 3:1) of the residue yielded 231 mg (0.5 mmol, 54%) 2-cyclopentyl-N-[2-[2-[[3-(trifluoromethyl)-phenyl]sulfonyl]-ethylsulfanyl]-pyridin-3-yl]acetamide. MS: m/z 473.1 [M+H]+.

Reference： [1]Patent: US2010/234428,2010,A1 .Location in patent: Page/Page column 13

27
[ 1123-00-8 ]
[ 101-77-9 ]
[ 1283594-65-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 25℃; for 12h;Inert atmosphere;	To a solution of N-ethyl-N'-[3-(dimethylamino)propyl]carbodiimide hydrochloride (144 mg, 0.75 mmol) and <strong>[1123-00-8]cyclopentylacetic acid</strong> (70 mg, 0.55 mmol) in CH2Cl2 (20 mL) was added 2a (50 mg, 0.25 mmol) at 25 C, and the mixture was stirred at that temperature for 12 h. The reaction mixture was poured into water (20 mL) and extracted with CH2Cl2 (20 mL × 2). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by GPC using CHCl3 as eluent to give 2h (65 mg, 0.16 mmol, 62%) as a colorless solid. Mp: 218-219 C (dec). 1H NMR (DMSO-d6): delta 1.13-1.20 (m, 4H), 1.49-1.62 (m, 8H), 1.70-1.76 (m, 4H), 2.18-2.27 (m, 6H), 3.80 (s, 2H), 7.10 (d, J = 8.1 Hz, 4H), 7.48 (d, J = 8.1 Hz, 4H), 9.77 (br, 2H). 13C NMR (DMSO-d6): delta 24.7, 32.1, 36.9, 40.2, 42.7, 119.4, 129.0, 136.2, 137.5, 170.9. IR (ATR): 1650 cm-1. MS (EI): m/z 418 (M+). Anal. Calcd for C27H34N2O2?0.25(H2O): C, 76.65; H, 8.22; N, 6.62. Found: C, 76.63; H, 8.19; N, 6.58.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1502 - 1507

28
[ 1123-00-8 ]
[ 1357096-05-9 ]
[ 1357096-68-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of the acid (0.12 mmole) in methanol (0.6 ml) was added at 0 C. 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride (0.12 mmole) and the solution was stirred for 60 min. The mixture was treated with the aniline I (0.12 mmole) and stirring was continued at 0 C. for 24 h. The mixture was evaporated and the residue partitioned between aqueous saturated Na2CO3 and ethyl acetate, the organic layer was dried and evaporated and the residue purified on prep. RP-18 HPLC using a gradient of acetonitrile and water (containing 0.1% of triethylamine) or NH2-silica using ethyl acetate/n-heptane to give the pure final product Ia.; The coupling of (S)-2-amino-6-(5-amino-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6-dihydropyrimidin-4(3H)-one (intermediate J) and <strong>[1123-00-8]cyclopentyl-acetic acid</strong> yielded the title compound as a white solid. MS (ESI): m/z=389.2 [M+H]+.
		Synthesis of the final product la from intermediate JGeneral procedureTo a solution of the acid (0.12 mmole) in methanol (0.6 ml) was added at 0C 4-(4,6- dimethoxy-l,3,5-triazin-2-yl)-4methyl-morpholinium chloride (0.12 mmole) and the solution was stirred for 60 min. The mixture was treated with the aniline I (0.12 mmole) and stirring was continued at 0C for 24 h. The mixture was evaporated and the residue partitioned between aqueous saturated Na2C03 and ethyl acetate, the organic layer was dried and evaporated and the residue purified on prep. RP-18 HPLC using a gradient of acetonitrile and water (containing 0.1 % of triethylamine) or NH2-silica using ethyl acetate/n-heptane to give the pure final product la.Example 26(S)-N-(3-(2-amino-l,4,5,5-tetramethyl-6-oxo-l,4,5,6-tetrahydropyrimidin-4-yl)-4- fluorophenyl)-2-cyclopentylacetamideThe coupling of (S)-2-amino-6-(5-amino-2-fluorophenyl)-3,5,5,6-tetramethyl-5,6- dihydropyrimidin-4(3H)-one (intermediate J) and <strong>[1123-00-8]cyclopentyl-acetic acid</strong> yielded the title compound as a white solid. MS (ESI): m/z = 389.2 [M+H]+.

Reference： [1]Patent: US2012/35195,2012,A1 .Location in patent: Page/Page column 35; 40
[2]Patent: WO2012/19966,2012,A1 .Location in patent: Page/Page column 93

29
[ 1123-00-8 ]
[ 1393912-02-1 ]
[ 1393912-01-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In chloroform; at 120℃;Microwave irradiation;	General procedure: To a mixture of 2-amino-5-(4-methylphenyl) thiophene-3-carboxamide 1a (0.25 g, 0.107 mol) and 4-benzyloxy benzoic acid 4a (0.319 g, 0.140 mol) in anhydrous chloroform (4 ml) was added triethylamine (0.32 g, 0.323 mol) and phosphonic acid cyclic anhydride (1.02 g, 0.323 mol). The reaction mixture was irradiated at 120 C in a microwave initiator for a given period of time (Table 1, entry 1). Once the substrate was completely consumed as monitored by TLC, the brown reaction mixture was cooled and poured into ice-cold water (10 ml). The product was extracted with ethyl acetate (2 × 25 ml) and the combined organic phase was washed with water, brine solution and dried over anhydrous sodium sulfite. The solvent was removed under vacuum and the brown residue was passed through a small plug of silica gel using petroleum ether/ethyl acetate (9/1) to afford 429 mg (94%) of 2a as a yellow solid.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 4639 - 4643

30
[ 1123-00-8 ]
[ 66315-16-0 ]
[ 1443759-62-3 ]

Yield	Reaction Conditions	Operation in experiment
76%		Intermediate 43: 2-Cyclopentylmethyl-l -methyl- 1 H-benzoimidazo le-5 -carboxylic acid 43.1 : 3-(2-Cyclopentyl-acetylamino)-4-methylamino-benzoic acid methyl ester 650 mg (5.07 mmol) cyclopentyl-acetic acid was stirred with 1.80 g (5.61 mmol) TBTU and 2.00 mL (14.4 mmol) TEA in 50 mL DMF at RT. After 30 min, 900 mg (5.00 mmol) 3-amino-4- methylamino-benzoic acid methyl ester was added and the mixture was stirred at RT for 3 h and at 50 C for 12h. The solvent was removed by distillation. The residue was taken up in aqueous potassium carbonate solution and water and extracted with EtOAc. The combined organic extracts were washed with water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuo. yield: 1.10 g (76 %) ESI-MS: m/z = 291 (M+H)+ Ri(TLC): 0.23 (DCM/MeOH = 19: 1)
76%		43.1: 3-(2-Cyclopentyl-acetylamino)-4-methylamino-benzoic acid methyl ester 650 mg (5.07 mmol) cyclopentyl-acetic acid was stirred with 1.80 g (5.61 mmol) TBTU and 2.00 mL (14.4 mmol) TEA in 50 mL DMF at RT. After 30 min, 900 mg (5.00 mmol) <strong>[66315-16-0]3-amino-4-methylamino-benzoic acid methyl ester</strong> was added and the mixture was stirred at RT for 3 h and at 50 C. for 12 h. The solvent was removed by distillation. The residue was taken up in aqueous potassium carbonate solution and water and extracted with EtOAc. The combined organic extracts were washed with water and saturated brine, dried over sodium sulfate, filtered and concentrated in vacuo. yield: 1.10 g (76%) ESI-MS: m/z=291 (M+H)+ Rf(TLC): 0.23 (DCM/MeOH=19:1)

Reference： [1]Patent: WO2013/87805,2013,A1 .Location in patent: Page/Page column 83
[2]Patent: US2013/158042,2013,A1 .Location in patent: Paragraph 0570; 0571; 0572; 0573; 0574

31
[ 1123-00-8 ]
[ 704902-18-1 ]
C₁₃H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃; for 24h;	General procedure: In each 200 muL well of a microtiter plate, a mixture of diisopropyl ethylamine (5.0 muL, 180.0mM solution in DMSO), HBTU (5 muL, 90mM solutionin DMSO), a carboxylic acid (10.0 muL, 30.0mM solution in DMSO) and a scaffold (compound 1and 2 ) (10.0muL, 30.0mM solution in DMSO) was shaken at rt for 24 h and analyzed by ESI-MS (or TLC) to verify the presence of the desired product. Each reaction mixture was diluted with H2O and transferred to another 96-well microtiter plate to make a 20 mM solution per each desired molecule (based on 100% conversion of amine) for the enzymatic assay directly without further purification.

Reference： [1]Chemistry - An Asian Journal,2013,vol. 8,p. 2600 - 2604
[2]European Journal of Medicinal Chemistry,2017,vol. 126,p. 1 - 6

32
[ 1123-00-8 ]
tert-butyl (1R,5S)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate [ No CAS ]
C₁₉H₃₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 12h;	General procedure: The appropriate carboxylic acid (1 mmol) and N-tboc-bispidine 13 (248 mg, 1.1 mmol) were dissolved in dry CH2Cl2 (5 mL) and cooled to 0 C. DMAP (6.1 mg, 0.05 mmol) and DCC (206 mg, 1 mmol) were added and the mixture was allowed to warm up and stir at rt. The precipitate was filtered off after 12 h and washed with cold CH2Cl2 (2 mL). The solvent of the filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (silica gel, mixtures of CH2Cl2 and MeOH-40:1. 20:1 or 9:1).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 7283 - 7308

33
[ 1123-00-8 ]
[ 1291986-72-5 ]
[ 1586791-37-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	To a solution of 16.41 g of <strong>[1123-00-8]cyclopentyl-acetic acid</strong> in 600 ml of dry DMF 17.30 g of HOBT, 24.54 g of EDC and 30 ml of DIPEA were added at 0C. After 1 h 27.51 g of 3-amino-4-(1 -ethyl-propylamino)-benzoic acid methyl ester and 30 ml of DIPEA were added and the reaction was stirred at rt for 16 h. The reaction was then poured into water and extracted with ethyl acetate three times. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulphate and concentrated. The crude product was purified by crystallization from diisopropylether to yield 29.35 g (73%) of 3-(2-cyclopentyl- acetylamino)-4-(1 -ethyl-propylamino)-benzoic acid methyl ester as an off-white solid. C20H30N2C*3 (346.47), LCMS (method 6_4_1 ): Rt = 2.04 min, m/z= 347.32 [M+H]+

Reference： [1]Patent: WO2014/44738,2014,A1 .Location in patent: Page/Page column 357

34
[ 1123-00-8 ]
(S)-tert-butyl (2-(5-(((2H-tetrazol-5-yl)methyl)carbamoyl)-3-cyclohexyl-2-oxoimidazolidin-1-yl)-2-oxoethyl)carbamate [ No CAS ]
(S)-N-((2H-tetrazol-5-yl)methyl)-1-cyclohexyl-3-(2-(2-cyclopentylacetamido)acetyl)-2-oxoimidazolidine-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Title compound (S)-N-((2H-tetrazol-5-yl)methyl)-1-cyclohexyl-3-(2-(2-cyclopentylacetamido)acetyl)-2-oxoimidazolidine-4-carboxamide (C6) was prepared from (S)-tert-butyl (2-(5-(((2H-tetrazol-5-yl)methyl)carbamoyl)-3-cyclohexyl-2-oxoimidazolidin-1-yl)-2-oxoethyl)carbamate and <strong>[1123-00-8]cyclopentyl acetic acid</strong> using method A in 2: 1 mixture DMF/CH2C12. 1H NMR (400 MHz, DMSO-<) delta 1.02-1.17 (3H, m), 1.22-1.41 (4H, m), 1.43-1.62 (6H, m), 1.63-1.79 (5H, m), 2.07-2.16 (3H, m), 3.27 (1H, dd, J=4, 10 Hz), 3.57 (1H, m), 3.68 (1H, t, J=10 Hz), 4.16 (1H, dd, J=5, 9 Hz), 4.47-4.56 (2H, m), 4.57-4.67 (2H, m), 7.98 (1H, t, J=6Hz), 8.98 (1H, t, J=6Hz), MS (LC/MS) m/z observed 460.95, expected 461.26 [M+H].
		General procedure: HC1 Solution in dioxane (4M, 5 ml) was added to respective carbamate compound (0.125 mmol) and stirred for 2 hrs at RT. The reaction mixture was concentrated to dryness under vacuum and swapped with MeOH (5 ml) three times. Resulting residue was dried well under vacuum and subjected to next reaction as it was. The residue obtained above, respective acid moiety (0.125 mmol), EDC (0.19 mmol), HOBt (0.16 mmol) and DIPEA (0.5 mmol) were stirred in anhydrous DCM (5 ml) for 16 hrs. The reaction mixture was concentrated under vacuum to give the crude product which was purified on a C18 column using 10-50% MeOH in water to yield product as an off-white solid (35-55%).

Reference： [1]Patent: WO2016/15160,2016,A1 .Location in patent: Page/Page column 66
[2]Patent: WO2017/132771,2017,A1 .Location in patent: Page/Page column 36; 52

35
[ 1123-00-8 ]
4-nitro-N-(4-[[4-(piperazin-1-yl)pyridin-2-yl]oxy]cyclohexyl)-3-(trifluoromethyl)aniline trifluoroacetate [ No CAS ]
2-cyclopentyl-1-(4-(2-(4-(4-nitro-3-(trifluoromethyl)phenylamino)cyclohexyloxy)pyridin-4-yl)piperazin-1-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃;	To a solution of <strong>[1123-00-8]2-<strong>[1123-00-8]cyclopentylacetic acid</strong></strong> (40 mg, 0.31 mmol) in dichloromethane (10 mL) was added DIEA (268 mg, 2.07 mmol), HATU (197 mg, 0.52 mmol), and 4-nitro-N-(4-[[4-( iperazin- l-yl)pyridin-2-yl]oxy]cyclohexyl)-3-(trifluoromethyl)aniline (TFA salt, 150 mg, 0.26 mmol). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of water (20 mL) and extracted with dichloromethane (10 mL). The organic layers were combined and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (2: 1). The product containing fractions were combined and concentrated under vacuum to provide 93.3 mg (63%) of 2-cyclopentyl-l-(4-(2-(4-(4-nitro-3- (trifluoromethyl)phenylamino)cyclohexyloxy)pyridin-4-yl)piperazin-l-yl) ethanone as a yellow solid. (ES, m/z): [M+H]+ 576; NMR (300 MHz, DMSO): delta 8.07 (d, J = 9.3 Hz, 1H), 7.80 (d, J = 6.0 Hz, 1H), 7.51 (d, J = 7.5 Hz, 1H), 7.10 (d, J = 2.1 Hz, 1H), 6.90 - 6.86 (m, 1H), 6.54 - 6.52 (m, 1H), 6.09 (d, J = 1.8 Hz, 1H), 5.09 - 4.85 (m, 1H), 3.61 - 3.52 (m, 5H), 3.38 - 3.20 (m, 3H), 2.13 (d, J = 7.8 Hz, 2H), 2.10 -1.99 (m, 5H), 1.98 - 1.88 (m, 2H), 1.78 - 1.36 (m, 9H), 1.16 - 1.09 (m, 2H).

Reference： [1]Patent: WO2016/118638,2016,A1 .Location in patent: Page/Page column 132; 133

36
[ 1123-00-8 ]
4-nitro-N-[4-[[2-(piperazin-1-yl)pyridin-4-yl]oxy]cyclohexyl]-3-(trifluoromethyl)aniline [ No CAS ]
2-cyclopentyl-1-[4-(4-[[4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]cyclohexyl]oxy]pyridin-2-yl)piperazin-1-yl]ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃;	Into a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[1123-00-8]2-<strong>[1123-00-8]cyclopentylacetic acid</strong></strong> (50 mg, 0.39 mmol) in dichloromethane (10 mL), HOBt (105 mg, 0.78 mmol, 2 eq.), EDCI (149 mg, 0.78 mmol, 2 eq.), triethylamine (118 mg, 1.17 mmol, 3 eq.), and 4-nitro-Ar-[4-[[2-(piperazin-l-yl)pyridin-4-yl]oxy]cyclohexyl]-3- (trifluoromethyl)aniline (181 mg, 0.39 mmol, 1 eq.). The resulting solution was stirred overnight at room temperature and then diluted with 20 mL of dichloromethane. The crude solution was washed with water and then with brine. The organic fraction was dried over anhydrous sodium sulfate and the solids were filtered off. The residue was applied onto a silica gel column and eluted with dichloromethane: methanol (30: 1). The product containing fractions were combined and concentrated under vacuum to provide 49.7 mg (22%) of as a yellow solid. (ES, m/z): [M+H]+ 576; NMR (300 MHz, CDC13): delta 8.08 - 8.01 (m, 2H), 6.91 - 6.87 (d, J = 2.7 Hz, 1H), 6.68 - 6.65 (dd, J = 2.4, 9.0 Hz, 1H), 6.35 - 6.33 (m, 1H), 6.13 (s, 1H), 4.53 (d, J = 7.5 Hz, 1H), 4.39 (br s, 1H), 3.77 - 3.65 (overlapping m, 6H), 3.48 (br s, 4H), 2.41 - 2.38 (leaning d, J = 7.2 Hz, 2H), 2.27 - 2.22 (m, 5H), 1.89 - 1.80 (m, 2H), 1.67 - 1.55 (m, 4H), 1.46 - 1.42 (m, 2H), 1.20 - 1.09 (m, 2H).

Reference： [1]Patent: WO2016/118638,2016,A1 .Location in patent: Page/Page column 138; 139

37
[ 1123-00-8 ]
ethyl 1-(6-amino-2-butoxy-5-nitropyrimidin-4-yl)-1,4-diazepane-2-carboxylate [ No CAS ]
ethyl 1-(6-amino-2-butoxy-5-nitropyrimidin-4-yl)-4-(2-cyclopentylacetyl)-1,4-diazepane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		A solution of <strong>[1123-00-8]2-<strong>[1123-00-8]cyclopentylacetic acid</strong></strong> (30 mg, 0.23 mmol) in DCM (5 mL) was treated with Et3N (0.11 mL, 0.78 mmol), EDC.HCI (67 mg, 0.35 mmol) and HOBt hydrate (47 mg, 0.35 mmol). The solution was stirred for 5 min followed by the addition of ethyl 1-(6-amino-2- butoxy-5-nitropyrimidin-4-yl)-1 ,4-diazepane-2-carboxylate 6b (89 mg, 0.23 mmol). The solution was allowed to stir overnight at room temperature. The reaction was quenched by addition of a saturated aqueous solution of NH4CI (50 mL). The phases were separated and the aqueous phase extracted with DCM (2 x 40 mL). The combined organic phases were dried over MgS04 and the solvent removed in vacuo to provide ethyl 1-(6-amino-2- butoxy-5-nitropyrimidin-4-yl)-4-(2-cyclopentylacetyl)-1 ,4-diazepane-2-carboxylate (91 mg, 79%) as a yellow oil; LC-MS (Method F) 493.5 [MH+]; RT 3.30 min.

Reference： [1]Patent: WO2017/1853,2017,A1 .Location in patent: Page/Page column 51

38
[ 623-03-0 ]
[ 1123-00-8 ]
3-(4-chlorophenyl)-5-(cyclopentylmethyl)-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: A solution of ArCN/NH2OH·HCl/DIPEA (1.05:1:3, 0.4 M,DMA) was introduced to a glass microreactor (250 muL) heatedat 100 C. The stream exiting from the first reactor wascombined with streams of the acid/DIPEA (1:1, 25.0 muL/min,0.5 M, DMA) and EDC/HOBt/DIPEA (1:1:1, 25 muL/min,0.6 M, DMA) in a second glass reactor (1.0 mL) at 150 C for15 min of residence time. This reaction was carried out with aback pressure of 4.0 bar. The reaction mixture was mixed withexcess water and extracted three times with dichloromethane.The combined organic layers were washed with brine, driedover magnesium sulfate, filtered, and concentrated and theresidue was purified via automated flash chromatography(SiO2) to afford the desired product (CombiFlash Rf, 12 gflash column). The solvent gradient was 90% hexane to 50%ethyl acetate over 15 min at a flow rate of 15 mL/min.

Reference： [1]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 239 - 246

39
[ 26947-41-1 ]
[ 1123-00-8 ]
5-(cyclopentylmethyl)-3-(isoquinolin-3-yl)-1,2,4-oxadiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		General procedure: A solution of ArCN/NH2OH·HCl/DIPEA (1.05:1:3, 0.4 M,DMA) was introduced to a glass microreactor (250 muL) heatedat 100 °C. The stream exiting from the first reactor wascombined with streams of the acid/DIPEA (1:1, 25.0 muL/min,0.5 M, DMA) and EDC/HOBt/DIPEA (1:1:1, 25 muL/min,0.6 M, DMA) in a second glass reactor (1.0 mL) at 150 °C for15 min of residence time. This reaction was carried out with aback pressure of 4.0 bar. The reaction mixture was mixed withexcess water and extracted three times with dichloromethane.The combined organic layers were washed with brine, driedover magnesium sulfate, filtered, and concentrated and theresidue was purified via automated flash chromatography(SiO2) to afford the desired product (CombiFlash® Rf, 12 gflash column). The solvent gradient was 90percent hexane to 50percentethyl acetate over 15 min at a flow rate of 15 mL/min.

Reference： [1]Beilstein Journal of Organic Chemistry,2017,vol. 13,p. 239 - 246

40
[ 606-23-5 ]
[ 1123-00-8 ]
2-(2-cyclopentylacetyl)-1H-indene-1,3(2H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	General procedure: In a 20 or 40 mL reaction vial equipped with magnetic stir bar and Teflon-lined cap, a solution of the corresponding carboxylic acid (1.5 mmol, 3.0 eq) and DMAP (183.3 mg, 1.5 mmol, 3.0 eq) in anhydrous DMF (9.0 mL) was homogenized by stirring for 5-10min. EDCI·HCl (287.6mg, 1.5mmol, 3.0 eq) was added, and the resulting mixture was homogenized by stirring for 5-10 min. The corresponding 1,3-indandione (0.5mmol, 1.0 eq) was added, and the resulting mixture was resealed and stirred for 12-72h, monitoring by LCMS. When complete, workup method A, B, or C was used to isolate the final products.

Reference： [1]Tetrahedron,2018,vol. 74,p. 2762 - 2768

41
[ 1123-00-8 ]
[ 517-89-5 ]
(R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl cyclopentylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10%		General procedure: A solution of shikonin in abs. CH2Cl2 (0.1 mmol/5 mL) was cooled to 0 C under argonatmosphere and DCC was added. DMAP was added after stirring for 15 min. After further stirring for15 min, the corresponding acid was added and stirring was continued for 14 h to 5 days with slowlywarming up to room temperature. After addition of 1 mL cyclohexane/0.1 mmol shikonin, the mixturewas concentrated under reduced pressure at room temperature to approx. 0.5 mL/0.1 mmol shikonin.The mixture was filtered over 3 mm silica and 2 mm celite (eluent: petroleum ether/CH2Cl2 = 1:0 to1:2). Product containing fractions were evaporated and submitted to flash CC and/or repeated PTLC(cyclohexane/CH2Cl2 mixtures). Due to the rapid decomposition of raw acylshikonin mixtures onevaporation to higher concentrations (c > approx. 0.2Macylshikonin) and degradation of acylshikoninson prolonged contact with silica, intermediate solutions were not to be concentrated to dryness and allisolation and purification steps had be performed at a good pace.

Reference： [1]Molecules,2018,vol. 23

42
[ 1123-00-8 ]
3-fluoro-N4-(4-(trifluoromethyl)benzyl)benzene-1,2,4-triamine [ No CAS ]
N-(2-amino-3-fluoro-4-(4-trifluoromethylbenzylamino)phenyl)cyclopentylacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45.4%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	Intermediate II (1.52 g, 5 mmol) and <strong>[1123-00-8]cyclopentyl acetic acid</strong> (0.582 ml, 5 mmol)Dissolved in dry dichloromethane (20ml), adding EDC to it(0.6 g, 5 mmol), DMAP (0.32 g, 2.0 mmol),The reaction was allowed to proceed overnight at room temperature with stirring. After the reaction is completed,The reaction solution was washed with water (20 ml × 3), and dichloromethane was evaporated under reduced pressure.The obtained solid dilute alcohol was recrystallized to give a white solid substance (i.e., compound 4) of 0.93 g.The yield is 45.4%.

Reference： [1]Patent: CN108707087,2018,A .Location in patent: Paragraph 0082; 0083; 0084; 0085

43
[ 1123-00-8 ]
(5-(3-chloro-4-hydroxybenzylidene)thiazolidine-2,4-dione) [ No CAS ]
((Z)-2- chloro-4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl 2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.1%		1 g (3.91 mmol) of 4a was added to a round- bottomed flask, and then, 0.49 1 g (3.91 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.04 g (0.33 mmol) of DMAP were added thereto, and then, the result was dissolved in dichloromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.742 g (3.60 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid.Yield: 89.1%1H NMR (300 MHz, DMSO-d6) 0 12.72 (s, 1H), o 7.85 (d, J=1.83 Hz, 1H), 07.80 (s, 1H), 07.61 (dd, J=8.43 and 1.83 Hz, 1H), 0 7.48 (d, J=8.43 Hz, 1H), 0 2.68 (d, J=7.32 Hz, 2H), 0 2.33 (m, J=7.32 Hz, 1H), 0 1.90 (m, 2H), o 1.66 (m, 4H), 0 1.30 (m, 2H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0146; 0147; 0148; 0149

44
(5-(3-bromo-4-hydroxybenzylidene)thiazolidine-2,4-dione) [ No CAS ]
[ 1123-00-8 ]
((Z)-2-bromo-4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl 2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.2%		1 g (3.33 mmol) of 19a was added to a round- bottomed flask, and then, 0.419 g (3.33 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.034 g (0.28 mmol) of DMAP were added thereto, and then, the result was dissolved in dichloromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.632 g (3.07 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid.Yield: 91.2%1H NMR (300 MHz, DMSO-d6) oe 12.73 (s, 1H), oe 7.99 (d, J=2.19 Hz, 1H), oe 7.80 (s, 1H), oe 7.64 (dd, J=8.43 and 2.19 Hz, 1H), oe 7.45 (d, J=8.43 Hz, 1H), oe 2.67 (d, J=7.32 Hz, 2H), oe 2.34 (m, J=7.32 Hz, 1H), oe 1.91 (m, J=6.96 Hz, 2H), oe 1.66 (m, J=6.96 Hz, 4H), oe 1.30 (m, J=6.96 Hz, 2H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0210; 0211; 0212; 0213

45
[ 911714-34-6 ]
[ 1123-00-8 ]
((Z)-4- ((2,4-dioxothiazolidin-5-ylidene)methyl)-2-methoxyphenyl-2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.7%		1 g (3.98 mmol) of 34a was added to a round- bottomed flask, and then, 0.5 g (3.98 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.04 g (0.33 mmol) of DMAP (4-(dim- ethylamino)pyridine) were added thereto, and then, the result was dissolved in dichloromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.755 g (3.66 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid.Yield: 81.7%1H NMR (300 MHz, DMSO-d6) 0 12.65 (s, 1H),0 7.80 (s, 1H), 0 7.37 (d, J=1.83 Hz, 1H), 0 7.26 (d, J=8.07 Hz, 1H), 07.19 (dd, J=8.07 and 1.83 Hz, 1H), 03.81 (s, 3H),o 2.59 (d, J=7.32 Hz, 2H), 02.32 (m, J=7.32 Hz, 1H), 0 1.88(m, J=6.96 Hz, 2H), 0 1.67 (m, 4H), 0 1.28 (m, J=6.96 Hz,2H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0274; 0275; 0276; 0277

46
[ 1123-00-8 ]
[ 1055980-74-9 ]
((Z)-4-((2,4-dioxothiazolidin-5-ylidene)methyl)-2-ethoxyphenyl 2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76.6%		1 g (3.77 mmol) of 49a was added to a round- bottomed flask, and then, 0.474 g (3.77 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.038 g (0.32 mmol) of 4-(dimethylamino) pyridine (DMAP) were added thereto, and then, the result was dissolved in dichioromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.7 16 g (3.47 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid.Yield: 76.6%1H NMR (300 MHz, DMSO-d6) 0 12.65 (s, 1H),o 7.79 (s, 1H), 0 7.34 (d, J=1.47 Hz, 1H), 0 7.24 (d, J=8.43 Hz, 1H), 0 7.17 (dd, J=8.43 and 1.47 Hz, 1H), 0 4.11 (m, J=6.96 Hz, 2H), 0 2.57 (d, J=7.32 Hz, 2H), 0 2.32 (m, J=7.32 Hz, 1H), 0 1.89 (m, 2H), 0 1.67 (m, 4H), 0 1.32 (t, J=6.96 Hz, 3H), 0 1.24 (m, 2H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0338; 0339; 0340; 0341

47
[ 103788-60-9 ]
[ 1123-00-8 ]
((Z)-4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl-2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.9%		1 g (4.52 mmol) of 64a was added to a round-bottomed flask, and then, 0.568 g (4.52 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.568 g (4.52 mmol) of DMAP (4- (dimethylamino)pyridine) were added thereto, and then, the result was dissolved in dichloromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.858 g (4.16 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid.Yield: 78.9%1H NMR (300 MHz, DMSO-d6) oe 12.64 (s, 1H),oe 7.80 (s, 1H), oe 7.70 (d, J=8.79 Hz, 2H), oe 7.30 (d, J=8.79 Hz, 2H), oe 2.62 (d, J=7.32 Hz, 2H), oe 2.32 (m, J=7.32 Hz, 1H), oe 1.88 (m, J=6.96 Hz, 2H), oe 1.68 (m, J=6.96 Hz, 4H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0402; 0403; 0404; 0405

48
[ 1123-00-8 ]
(5-(2-chloro-3-hydroxybenzylidene)thiazolidine-2,4-dione) [ No CAS ]
((Z)-2-chloro-3-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl-2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.6%		1 g (3.91 mmol) of 79a was added to a round- bottomed flask, and then, 0.49 1 g (3.91 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.04 g (0.33 mmol) of DMAP were added thereto, and then, the result was dissolved in dichloromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.742 g (3.60 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid.Yield: 75.6%1H NMR (300 MHz, DMSO-d6) oe 12.81 (s, 1H), oe 7.89 (s, 1H), oe 7.60 (t, J=8.07 Hz, 1H), oe 7.50 (dd, J=8.07 and 1.47 Hz, 1H), oe 7.44 (dd, J=8.07 and 1.47 Hz, 1H), oe2.68 (d, J=7.32 Hz, 2H), oe 2.36 (m, J=7.32 Hz, 1H), oe 1.90 (m, 2H), oe 1.68 (m, 4H), oe 1.30 (m, 2H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0466; 0467; 0468; 0469

49
[ 1123-00-8 ]
(5-(2-chloro-4-hydroxybenzylidene)thiazolidine-2,4-dione) [ No CAS ]
((Z)-3-chloro-4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl-2-cyclopentylacetate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.7%		1 g (3.91 mmol) of 94a was added to a round- bottomed flask, and then, 0.49 1 g (3.91 mmol) of <strong>[1123-00-8]cyclopentylacetic acid</strong> and 0.04 g (0.33 mmol) of DMAP were added thereto, and then, the result was dissolved in dichloromethane (20 ml), followed by stirring in an ice bath. After 5 minutes, 0.742 g (3.60 mmol) of N, N?-dicyclohexylcarbodiimide (DCC) was added thereto and reacted at room temperature. When the reaction was completed, which was confirmed by TLC, the resulting urea in the form of solid was filtered under reduced pressure, and the filtrate was subjected to acid-base extraction and recrystallization, thereby obtaining pure solid. Yield: 88.7%1H NMR (300 MHz, DMSO-d6) oe12.78 (s, 1H),oe7.88 (s, 1H), oe7.63 (d, J=8.4 Hz, 1H), oe7.54 (d, J=2.19 Hz,1H), oe7.34 (dd, J=8.4 and 2.19 Hz, 1H), oe2.62 (m, J=7.68Hz, 2H), oe2.29 (m, J=7.68 Hz, 1H), oe1.88 (m, 2H), oe1.62 (m,4H), oe1.28 (m, 2H)

Reference： [1]Patent: US2019/16695,2019,A1 .Location in patent: Paragraph 0531; 0532; 0533; 0534

50
[ 1123-00-8 ]
[ 5763-55-3 ]

Reference： [1]Organic Letters,2019
[2]Tetrahedron,2019,vol. 75,p. 3186 - 3194
[3]Organic Letters,2020,vol. 22,p. 997 - 1002

51
[ 766-00-7 ]
[ 1123-00-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1-hydroxycyclohexyl phenyl ketone; sodium hydroxide In 1,2-dimethoxyethane at 80℃; Sealed tube; chemoselective reaction;

Reference： [1]Tan, Wen-Yun; Lu, Yi; Zhao, Jing-Feng; Chen, Wen; Zhang, Hongbin [Organic Letters, 2021, vol. 23, # 17, p. 6648 - 6653]

52
[ 1123-00-8 ]
[ 1122-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C 2: tetrahydrofuran / 0 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO LTD - CN113121609, 2021, A

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1123-00-8	MDL No. :	MFCD00001387
Formula :	C₇H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YVHAIVPPUIZFBA-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	71606
Synonyms :

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.42
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) :	-5.87 cm/s

Log Po/w (iLOGP) :	1.56
Log Po/w (XLOGP3) :	1.71
Log Po/w (WLOGP) :	1.65
Log Po/w (MLOGP) :	1.23
Log Po/w (SILICOS-IT) :	1.36
Consensus Log Po/w :	1.5

[ CAS No. 1123-00-8 ] {[proInfo.proName]}

Quality Control of [ 1123-00-8 ]

Related Doc. of [ 1123-00-8 ]

Product Details of [ 1123-00-8 ]

Calculated chemistry of [ 1123-00-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1123-00-8 ]

Application In Synthesis of [ 1123-00-8 ]

[ 1123-00-8 ] Synthesis Path-Downstream 1~52

Related Functional Groups of
[ 1123-00-8 ]

Aliphatic Cyclic Hydrocarbons

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Log S (ESOL) :	-1.58
Solubility :	3.37 mg/ml ; 0.0263 mol/l
Class :	Very soluble
Log S (Ali) :	-2.11
Solubility :	0.997 mg/ml ; 0.00778 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.78
Solubility :	21.5 mg/ml ; 0.167 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

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:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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.
P211	Do not spray on an open flame or other ignition source.
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.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
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