[ CAS No. 141109-14-0 ] {[proInfo.proName]}

Name: 141109-14-0|Methyl (S)-2-amino-2-(2-chlorophenyl)acetate|98%
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Quality Control of [ 141109-14-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 141109-14-0 ]

Product Details of [ 141109-14-0 ]

CAS No. :	141109-14-0	MDL No. :	MFCD15071471
Formula :	C₉H₁₀ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UTWOZNRDJNWTPS-QMMMGPOBSA-N
M.W :	199.63	Pubchem ID :	11745652
Synonyms :

Calculated chemistry of [ 141109-14-0 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.02
TPSA :	52.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	1.53
Log Po/w (WLOGP) :	1.19
Log Po/w (MLOGP) :	1.67
Log Po/w (SILICOS-IT) :	1.66
Consensus Log Po/w :	1.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	1.3 mg/ml ; 0.00653 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	1.16 mg/ml ; 0.00579 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.78
Solubility :	0.328 mg/ml ; 0.00164 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 141109-14-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 141109-14-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 141109-14-0 ]
Downstream synthetic route of [ 141109-14-0 ]

[ 141109-14-0 ] Synthesis Path-Upstream 1~1

1
[ 141109-14-0 ]
[ 144750-52-7 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 10, p. 1387 - 1396

[ 141109-14-0 ] Synthesis Path-Downstream 1~44

1
L-(+)-tartaric acid salt of α-amino-(2-chlorophenyl)acetic acid methyl ester [ No CAS ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In dichloromethane; water at 5℃; for 1.66667h;	4 240 liters of demineralised water, 240 liters of dichloromethane and 120 kg of the L-(+)-tartaric acid salt of α-amino-(2-chlorophenyl)-acetic acid methyl ester of Formula III were charged into a clean and dry reactor followed by stirring at about 30° C. for about 10 minutes. The resultant reaction solution was cooled to about 5° C. followed by adjusting the pH to about 7.46 by the addition of 900 liters of 10% sodium bicarbonate solution at about 5° C. over about 1 hour, 40 minutes. Organic and aqueous layers were separated and the aqueous layer was extracted with 2×60 liters of dichloromethane. Both the organic layers were combined and the organic layer was washed with 3×120 liters of demineralised water followed by separation of organic and aqueous layers. Organic layer was distilled completely at about 30° C. over about 3.5 hours to afford a residue of the free base of Formula II. To the residue, 138.4 liters of toluene, 179.7 kg of dipotassium hydrogen phosphate and 118.2 kg of 2-(2-thiophene)ethanol tosylate of Formula VII were charged into a clean and dry reactor followed by heating to about 92.5° C. and maintained for about 30 hours. The reaction mass was cooled to 30° C. followed by charging 203 liters of toluene and 600 liters of water. The resultant reaction suspension was stirred for about 30 minutes followed by separation of organic and aqueous layers. The aqueous layer was extracted with 72 liters of toluene followed by separation of organic and aqueous layers. Both the organic layers were combined and the total organic layer was washed with 143 liters of water. Organic and aqueous layers were separated and to the organic layer 34.2 liters of 12 N hydrochloric was charged at about 12.5° C. followed by stirring for about 30 minutes. The resultant reaction mixture was heated to about 55° C. followed by stirring for about 15 minutes. Separated solid was filtered and the solid was washed with 69 liters of toluene. The wet reaction material was transferred into a reactor followed by the charging of 420 liters of acetone and 30.4 liters of 12N hydrochloric acid. The resultant reaction suspension was heated to about 58° C. followed by stirring for about 20 minutes. The above reaction solution was cooled to about 11° C. for about 45 minutes. The solid that formed was separated in a centrifuge and the solid was washed with 60 liters of acetone. Finally the solid was subjected to spin drying for about 1.5 hours followed by drying at about 62.5° C. under vacuum for about 7 hours to afford 75 kg (yield: 63.25%) of the title compound.

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - US2007/225320, 2007, A1 Location in patent: Page/Page column 5

2
[ 40412-06-4 ]
[ 141109-14-0 ]
[ 141109-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; at 78 - 82℃; for 8 - 10h;Product distribution / selectivity;	Example (4); Preparation of methyl(2S)-(2-chIorophenyl)(6,7-dihydrothieno[3,2-clpyridin- 5(4H)-vDacetate using free base of methyl (25r)-amino-(2-chlorophenv?acetate; A mixture of methyl(25)-amino-(2-chlorophenyl)acetate freebase (10 gm, 0.05 mole) and 2-(2-thienyl)ethyl-4-methylbenzenesulfonate (14.1 gm, 0.05 mole ) was refluxed at 78C to 82C in the presence of triethylamine (5.0 volumes) for 8 to 10 hrs. After completion of the reaction, ethyl acetate was added to the contents of reaction mass, stirred for 10 to 15 mins. and the solid was filtered. The ethyl acetate solution was distilled off completely under vacuum, dissolved the residue in methylenedichloride, washed with water followed by saturated sodium chloride solution, dried and distilled completely to get methyl(25)-(2-chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)- yl)acetate (7.2 gm) as residue. To the residual liquid aqueous formaldehyde (30%, 36 ml) was added and heated to 600C to get clear solution and maintained for 20 to 30 mins. After completion of reaction, water and methylenedichloride were added and the peta was adjusted between 7 to 8 by using solid sodium bicarbonate. Layer of methylenedichloride was separated, dried and evaporated to get methyl(2<S)-(2- <n="9"/>chlorophenyl)(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate (4.7 gm ).Yield = 29% and etaPLC Purity = 98.6%.

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 2136 - 2141
[2]Patent: WO2007/144729,2007,A1 .Location in patent: Page/Page column 5; 7-8

3
[ 40412-06-4 ]
[ 141109-14-0 ]
methyl [2-(thien-2-yl)ethylamino](2-chlorophenyl)-acetate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; potassium iodide; In acetonitrile; at 30 - 80℃; for 24h;Heating / reflux;	In (750 ml) acetonitrile at about 30-35C, (150g) DL-2-(2-chlorophenyl)glycine methyl ester is added followed by addition of (191 g) 2(2-thiophen.e)emanol tosylate, (76g) sodium bicarbonate and (12.5g) potassium iodide. The reaction mixture is refluxed at about 80C under vigorous stirring for 24 hours, (12.5g) potassium iodide is added and refluxed further for 24 hours. The solvent is distilled off completely under vacuum at 45-50C and the residual mass is degassed at 50-55C under vacuum for 30 minutes. It is dissolved in (2250ml) ethyl acetate at 30-35C and (750ml) water is added. The upper product enriched layer is washed with aq NaCl 10% soln and cooled to 0-5C. To this ethyl acetate layer is added con HC1 acid (110 ml con HC1 acid in 210ml of chilled water) at 0-5C with stirring and maintain for 2 hours. The product is filtered and washed with chilled ethyl acetate (2x15 Oml) and sucked to dryness. The product cake is washed with (2xl50ml) hexane and suck to maximum dryness and dried at 45-55C. (175g)

Reference： [1]Patent: WO2004/108665,2004,A2 .Location in patent: Page 13

Yield	Reaction Conditions	Operation in experiment
		4 Methyl (+)-(S)-α-(2-thienyl-2-ethylamino)-α-(2-chlorophenyl)acetate hydrochloride EXAMPLE 4 Methyl (+)-(S)-α-(2-thienyl-2-ethylamino)-α-(2-chlorophenyl)acetate hydrochloride 1 g of sodium borohydride is suspended in 100 ml of dichloromethane, under cooling (water bath of 14 to 15° C.) and with magnetic stirring. 4.5 ml of acetic acid are then slowly added over 5 to 10 minutes. As soon as the release of hydrogen is complete, the dichloromethane is completely evaporated at reduced pressure and the residue obtained is then dissolved in the acetic solution of methyl (+)-(S)-α-amino-α-(2-chlorophenyl)acetate obtained in Preparation f) above.

5
[ 40412-06-4 ]
[ 141109-14-0 ]
(S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		(+)-o-chlorophenylglycine methyl ester (140 g, 0.70 mol) was sequentially added to a 1 L three-necked flask,(0.70 mol) of alpha-2-thiopheneethanol-p-toluenesulfonate and 420 ml of acetonitrile,118 g (1.4 mol) of sodium hydrogencarbonate was added with stirring,Potassium iodide 5g, stirring heated to 85 C, reaction 27h, Filtration, filter cake washed with acetonitrile to white, combined with acetonitrile, back into the three-necked flask, Stirring at room temperature with concentrated hydrochloric acid adjusted to pH = 1 ~ 4, continue stirring more than 2 hours, Filtration, cake drying 40 C 5h,(1-alpha - (2-thienylethylamino) -2- (2-chlorophenyl) acetate hydrochloride (IX)Weighing 155g, purity> 99%The filtrate was concentrated to dryness under reduced pressure and the acetonitrile solvent was recovered to give a yellow solid. Ethyl acetate (300 ml) was added and the mixture was stirred for 1 h.Filtration, filter cake with the right amount of ethyl acetate wash,Dried to give (+) - alpha- (2-thienylethylamino) -2- (2-chlorophenyl) acetic acid methyl ester hydrochloride (IX), Weighed 70g, purity> 95%, The 70 g of the solid was dissolved by stirring with 0. 8 times by weight of methanol under reflux,After the addition of 3. 6 times by weight of ethyl acetate, the crystals were separated and the temperature was lowered to room temperaturefilter,To obtain a purified product of (+) - alpha- (2-thienylethylamino) -2- (2-chlorophenyl) acetic acid methyl ester hydrochloride (IX)After drying, 65 g of white crystals were obtained,Purity & gt; 99%The purification yield was 92.8%. The filtrate was concentrated to dryness under reduced pressure, and ethyl acetate was recovered, the total yield of the reaction was 91%.
66.3%		1.80 liters of tertiary-butyl acetate and 134.10 kg of dipotassium hydrogen phosphate were to S-(+)-isomer of methyl alpha-amino-(2-chlorophenyl)acetate of Formula II obtained from Example 4 at a temperature of about 30 C. 0.892 kg of 2-(2-thiophene)ethanol tosylate of Formula VII obtained from Example 5 were then added and the reaction mass was subjected to heating to a temperature of about 92.5 C. and maintained for about 24 hours followed by distilling of the solvent at a temperature below 60 C. under a vacuum of about 650 mm Hg. The obtained reaction mass was cooled to a temperature of about 12.5 C. and 2.52 liters of ethyl acetate and 2.52 liters of water were added. The mass was subjected to stirring for about 10 minutes and the solution was allowed to settle for about 15 minutes, followed by separating the aqueous layer from organic layer. The aqueous layer was extracted with ethyl acetate (2×1.8 liters). The organic layer was washed with demineralised water (3×1.12 liters). Organic layer was cooled to a temperature of about 12.5 C., and 280 ml of 36% aqueous hydrochloric acid was slowly added. The reaction mixture was stirred for about 25 minutes. The obtained reaction mass was filtered, and the solid was washed with 560 ml of ethyl acetate and subjected to spin-drying. The wet solid was transferred into a reactor followed by the addition of 2.24 liters of ethyl acetate and the mass was subjected to heating to a temperature of about 77 C. for about 75 minutes. The mass was cooled to 27.5 C. over a period of about 75 minutes, filtered and the solid washed with 560 ml of ethyl acetate. Finally the solid was subjected to spin drying followed by drying at a temperature of about 62.5 C. under vacuum of about 600 mm Hg over a period of 4 hours and cooled to a temperature of about 30 C. to afford 65 kg (yield: 66.3%) of title compound
45%		Example (1); Preparation of methvK2-y)-(+)-(2-chIorophenyl)-N-r2-(2-thieno)ethyllgIycinate using free base of methyl (2.y)-(+)-amino-(2-chIorophenvI')acetate; A mixture of methyl(25)-amino-(2-chlorophenyl)acetate freebase (10gm, 0.05mole) and 2-(2-thienyl)-ethyl-4-methylbenzenesulfonate (14 gm, 0.05mole) was refluxed at 78C to 82C in the presence of triethylamine (5.0 volumes) for 8 tolO hrs. After completion of the reaction, ethyl acetate was added to the reaction mass, stirred for 10 to 15 mins. and solid was filtered off. The ethyl acetate solution was distilled completely under vacuum, dissolved the residue in methylenedichloride and washed with water followed by saturated sodium chloride solution, dried and distilled completely to get methyl(2S)-(+)-(2-chlorophenyl)-N-[2-(2-thieno) ethyl] glycinate as free base (6.9 gm). This is treated with a solution of isopropyl alcohol hydrochloride to get methyl(2S)-(+)-(2-chlorophenyl)-N-[2-(2-thieno)ethyl]glycinate hydrochloride salt (7.8 gm) Yield = 45% and HPLC Purity = 98.2%

		EXAMPLE 4; (+)-Methyl alpha-(2-thienyl ethyl amino)-(2-chlorophenyl)acetate hydrochloride: 50 Kg of (+)-2-chlorophenyl glycine methyl ester was dissolved in acetonitrile (250 lit). To this solution, potassium bicarbonate (75 Kg) and 2-thienyl ethyl para toluene sulphonate (100 Kg) was added at 25-30 C. The reaction mass was heated upto 78-80 C. and maintained for 40 hours. The solvent was distilled off under reduced pressure to yield a residue. To this residue, water (75 lit) and ethyl acetate (250 lit) were added and stirred for 1 hour. The organic layer was separated, added hydrochloric acid (30% solution; 25 lit) to the reaction mass till the pH of 1.2-1.5 attained. The reaction mass was centrifuged to obtain (+)-methyl alpha-(2-thienyl ethyl amino)-(2-chlorophenyl)acetate hydrochloride in a crude form. The product was dried and subjected to crystallization in a mixture of toluene-methanol (4:1) ratio to achieve 99.5% enantiomeric purity.Yield: 65 Kg.[alpha]D/20=+110-112 (c=1 in methanol).Enantiomeric purity: 99.5%
		240 liters of demineralised water, 240 liters of dichloromethane and 120 kg of the L-(+)-tartaric acid salt of alpha-amino-(2-chlorophenyl)-acetic acid methyl ester of Formula III were charged into a clean and dry reactor followed by stirring at about 30 C. for about 10 minutes. The resultant reaction solution was cooled to about 5 C. followed by adjusting the pH to about 7.46 by the addition of 900 liters of 10% sodium bicarbonate solution at about 5 C. over about 1 hour, 40 minutes. Organic and aqueous layers were separated and the aqueous layer was extracted with 2×60 liters of dichloromethane. Both the organic layers were combined and the organic layer was washed with 3×120 liters of demineralised water followed by separation of organic and aqueous layers. Organic layer was distilled completely at about 30 C. over about 3.5 hours to afford a residue of the free base of Formula II. To the residue, 138.4 liters of toluene, 179.7 kg of dipotassium hydrogen phosphate and 118.2 kg of 2-(2-thiophene)ethanol tosylate of Formula VII were charged into a clean and dry reactor followed by heating to about 92.5 C. and maintained for about 30 hours. The reaction mass was cooled to 30 C. followed by charging 203 liters of toluene and 600 liters of water. The resultant reaction suspension was stirred for about 30 minutes followed by separation of organic and aqueous layers. The aqueous layer was extracted with 72 liters of toluene followed by separation of organic and aqueous layers. Both the organic layers were combined and the total organic layer was washed with 143 liters of water. Organic and aqueous layers were separated and to the organic layer 34.2 liters of 12 N hydrochloric was charged at about 12.5 C. followed by stirring for about 30 minutes. The resultant reaction mixture was heated to about 55 C. followed by stirring for about 15 minutes. Separated solid was filtered and the solid was washed with 69 liters of toluene. The wet reaction material was transferred into a reactor followed by the charging of 420 liters of acetone and 30.4 liters of 12N hydrochloric acid. The resultant reaction suspension was heated to about 58 C. followed by stirring for about 20 minutes. The above reaction solution was cooled to about 11 C. for about 45 minutes. The solid that formed was separated in a centrifuge and the solid was washed with 60 liters of acetone. Finally the solid was subjected to spin drying for about 1.5 hours followed by drying at about 62.5 C. under vacuum for about 7 hours to afford 75 kg (yield: 63.25%) of the title compound.
		To methyl (+)-(S)-alpha-amino(2-chlorophenyl)acetate hydrochloride (120 g) in water (200 mL) and toluene (500 mL) was added NaHCO3 and stirred at 25 to 300C and the layers were separated. To the organic layer was added water, stirred and the layers were separated. To the organic layer containing methyl (+)- alpha-amino(2-chlorophenyl)acetate was added (2-thienyl)ethyl-p-toluenesulphonate (180 gm); K2HPO4 (280 gm) and catalyst (10 g) and heated to 85 to 900C for about 15 - 20 hrs. After completion of the reaction; toluene was distilled out completely and the reaction mass was cooled followed by the addition of ethyl acetate and DM water. The reaction mass was stirred and the layers were separated. To organic layer methanol (50 mL) was added followed by 53 gm of 35% Con. HCl. The solid obtained was filtered and washed with ethyl acetate and dried under vacuum to yield methyl-(+)-alpha-(2-thienylethylamino)(2- chlorophenyl)acetate hydrochloride. (Yield: 105 g).
		Into a three-necked flask, compound 4 28 g, compound 2 48 g, and potassium carbonate 29 g were added.6.4ml of water, stirred and heated to 100-106 C for 14h,Filtration under cooling, the filtrate was added dropwise with 36% concentrated hydrochloric acid to pH = 1-2, and filtered.The filter cake was dried to give(S)-2-(2-thienylethylamino)(2-chlorophenyl)acetic acid methyl ester hydrochloride;Prepare the molecular formula as follows:

Reference： [1]Patent: CN103467486,2016,B .Location in patent: Paragraph 0103-0105
[2]Patent: US2007/225320,2007,A1 .Location in patent: Page/Page column 7
[3]Patent: WO2007/144729,2007,A1 .Location in patent: Page/Page column 6
[4]Patent: US2007/191609,2007,A1 .Location in patent: Page/Page column 4
[5]Patent: US2007/225320,2007,A1 .Location in patent: Page/Page column 5
[6]Patent: WO2011/12961,2011,A1 .Location in patent: Page/Page column 7
[7]Patent: CN108707156,2018,A .Location in patent: Paragraph 0006; 0008

6
[ 87-69-4 ]
[ 141109-14-0 ]
[ 141109-15-1 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; acetone; at 20 - 55℃; for 28 - 32h;	EXAMPLE 2; (+) tartrate salt of 2-chlorophenyl glycine methyl ester: Methyl alpha amino(2-chlorophenyl)acetate (100 Kgs) was dissolved in acetone (72 lit). This solution was added to a suspension of L(+)-tartaric acid in methanol (400 lit) at 30-35 C. The reaction mass was stirred for 12 hours. The mass was cooled to 20-22 C. when solid was observed. The mass was again heated to 50-55 C.; kept for 2 hours and cooled again to 20-22 C. An aliquot sample was taken and tested for the melting range and enantiomeric purity. The process of heating and cooling was repeated for 8-10 times till the desired enantiomeric purity is achieved. (>99%). 87 Kgs of (+) tartrate salt of 2-chlorophenyl glycine methyl ester was obtained with enantiomeric purity of 99.0% and above.[alpha]D/20=+95.5 (c=1 in methanol)M.P.=167 to 170 C.
	With acetophenone; In methanol; acetone; at 28 - 32℃; for 20h;Green chemistry;Catalytic behavior;	To a 100 ml three-mouth flask , added L - (+) - tartaric acid (6.6 g, 0 . 044 muM) and anhydrous methanol (80 ml), stirring at room temperature to dissolve all, adding 0.4 g (0.003 muM) acetophenone, then a mixed solution of o-chlorophenylglycine methyl ester (8.0 g, 0.04 mol) and 16 ml of a solvent (a solvent is a mixture of acetone and methanol, and a volume ratio of acetone to methanol of 1:5) is dropwise added to the reactor, During the addition process, solids precipitated and took about 4 hours. (During the liquid chromatography, column chromatography or thin-plate chromatography, the reaction was monitored, and the progress of the reaction was judged by liquid chromatography, column chromatography or thin-plate chromatography with DeltaRf value, and the DeltaRf value was 1.38; During the reaction, liquid chromatography, column chromatography or thin layer chromatography was carried out, capillary sampling was carried out 2 to 3 mm, and spot plate expansion measurement was carried out, R-(-)-o-chlorophenylglycine methyl ester tartrate is dissolved in the solvent and is rapidly developed on the plate or on the column; while S-(+)-o-chlorophenylglycine methyl tartrate is highly polar Cannot be unfolded in solvent and left at the origin; Do not measure the unfolding value of the solvent 0 and R-(-)-o-chlorophenylglycine methyl ester tartrate expansion value 1, S- (+)-o-chlorophenylglycine methyl ester tartrate expansion value 2, R- (-)- O-chlorophenylglycine methyl ester tartrate expansion value 1 / solvent expansion value 0 is Rf1; The S-(1)-o-chlorophenylglycine methyl ester tartrate expansion value 2/solvent expansion value of 0 is Rf2; Rf1-Rf2= DeltaRf, DeltaRf is the difference between S-(+)-o-chlorophenylglycine methyl ester tartrate and R-(-)-o-chlorophenylglycine methyl ester tartrate Rf, The developing agent was acetone and methanol, and the ratios of the two were continuously adjusted during the experiment. When the volume ratio of acetone to methanol reaches a certain ratio, the difference between the S-(+)-o-chlorophenylglycine methyl ester tartrate and the R-(-)-o-chlorophenylglycine methyl ester tartrate Rf is the largest and the value is no longer changed. The Rf value is the ratio between the developed height of the developed object and the "difference between the solvent front and the solvent starting point" in thin plate chromatography; The difference between the two comparative compounds Rf is the A Rf value, which reflects the difference in the "adsorption-desorption" ability between the two unfolded materials under the selected developer conditions. When the volume ratio of acetone to methanol was 1:5, the difference between S-(+)-o-chlorophenylglycine methyl ester tartrate and R-(i)-o-chlorophenylglycine methyl ester tartrate Rf was 1.38.) After the completion of the dropwise addition, the reaction was carried out for 15 to 16 hours under the conditions of a temperature of 28 to 32 C. After the reaction, the mixture was cooled, and stirring was continued for one hour. Due to the continuous precipitation of S-(+)-o-chlorophenylglycine methyl ester tartrate which is insoluble under the solvent conditions, was subjected to suction filtration, the filter cake was dried to obtain a dry solid S-(+)-o-chlorophenylglycine methyl ester tartrate, and the mother liquor was continuously fed into the reaction as a solvent, which was less than 16 ml of the present example, the supplemental solvent acetone-methanol ratio is unchanged. When using the mother liquor as a solvent for separation, pay attention to the dosage. The mother liquor was repeatedly used in the experiment three times in the experiment. Total yield 86%

Reference： [1]Patent: US2007/191609,2007,A1 .Location in patent: Page/Page column 4
[2]Patent: CN109734617,2019,A .Location in patent: Paragraph 0057; 0058; 0071; 0074; 0075

7
[ 141109-15-1 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In methanol; for 0.5h;Reflux;	<strong>[141109-15-1]d-(+)-o-chlorophenylglycine methyl ester tartrate</strong>, 500g of methanol and 2L of methanol were sequentially added to the 3-necked flask, and the mixture was heated and refluxed for about 0.5 hours. The solution was completely dissolved and cooled to room temperature, The filter cake was dried at 40 C for 5 h and weighed to 450 g. The yield was 90%. The optical rotation was [alpha] D / 20 = + 92.5 .The filtrate was concentrated to dryness under reduced pressure to give a white solid which was dried at 40 C for 5 h and weighed to 47 g. The solid had lower optical rotation as the next batch of the starting material.<strong>[141109-15-1]d-(+)-o-chlorophenylglycine methyl ester tartrate</strong> 350g ([alpha] D / 20 = + 92.5 ) and 1500ml of purified water were sequentially added to the 5L measuring cup, stirred and dissolved until 1000ml of methylene chloride was completely dissolved, Stirring with sodium carbonate adjusted to pH = 7 ~ 8, standing stratification, water layer with dichloromethane extraction, combined methylene chloride layer, washed, dried methylene chloride layer with anhydrous sodium sulfate 2h, filtered desiccant The dichloromethane layer was concentrated to constant weight to give a pale yellow oil (Compound V). 181 g of the product was weighed and the yield was 95%.
	With ammonia; In dichloromethane; water; for 0.5h;pH 7.0 - 7.2;	EXAMPLE 3; (+)-2-chlorophenyl glycine methyl ester: (+) Tartrate salt of 2-chlorophenyl glycine methyl ester (90 Kgs) was mixed with water (450 lit) and treated with ammonia solution (20%; 45 lit) till the pH of the reaction mass in the range of 7.0-7.2. Dichloromethane (270 lit) was added and stirred for 30 minutes. The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 lit) twice. The organic layers are combined and distilled the solvent under reduced pressure to obtain the product, (+)-2-chlorophenyl glycine methyl ester (47 Kg) as oily residue.
	With sodium hydroxide; In water; toluene; at 0 - 10℃;pH 9;	In a three-necked flask, put (+)-o-chlorophenylglycine methyl ester L-(+) tartrate 50g, 150ml of toluene, stir and cool to 0-10 C, add 5% aqueous sodium hydroxide solution to pH=9, static The layers were separated, and the aqueous phase was extracted once with 100 ml of toluene. The organic layer was combined, and toluene was evaporated under reduced pressure to give (+)-o-chlorophenylglycine methyl ester as a brown-yellow oil;

Reference： [1]Patent: CN103467486,2016,B .Location in patent: Paragraph 0093-0095
[2]Patent: US2007/191609,2007,A1 .Location in patent: Page/Page column 4
[3]Patent: CN108707156,2018,A .Location in patent: Paragraph 0006; 0008

8
[ 67-56-1 ]
[ 1198213-98-7 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: methanol With sulfuric acid Cooling with ice; Reflux; Stage #2: (S)-2-(2-chlorophenyl)glycinamide hydrochloride at 20℃; Reflux; Stage #3: With sodium hydroxide In water

9
[ 865187-82-2 ]
[ 141109-14-0 ]
[ 113665-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In acetonitrile Reflux;
	Stage #1: 2-(2-bromoethyl)-3-(bromomethyl)thiophene; methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate In ethyl acetate; acetonitrile at 25 - 30℃; for 0.25h; Stage #2: With N-ethyl-N,N-diisopropylamine In ethyl acetate; acetonitrile Reflux;

Reference： [1]Location in patent: experimental part Van Der Meijden, Maarten W.; Leeman, Michel; Gelens, Edith; Noorduin, Wim L.; Meekes, Hugo; Van Enckevort, Willem J.P.; Kaptein, Bernard; Vlieg, Elias; Kellogg, Richard M. [Organic Process Research and Development, 2009, vol. 13, # 6, p. 1195 - 1198]
[2]Sashikanth, Suthrapu; Raju, Veeramalla; Somaiah, Sripathi; Rao, Peddisrinivasa; Reddy, Karnativenugopal [Synthesis, 2013, vol. 45, # 5, p. 621 - 624]

10
[ 141109-14-0 ]
[ 1193342-88-9 ]
[ 1193343-40-6 ]

Yield	Reaction Conditions	Operation in experiment
59.4%	Stage #1: 5-(2-methylbenzothiazol-5-yloxymethyl)isoxazole-3-carboxylic acid With dmap; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 0.5h; Molecular sieve; Stage #2: methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide

Reference： [1]Location in patent: experimental part Huang, Qingqing; Mao, Jialin; Wan, Baojie; Wang, Yuehong; Brun, Reto; Franzblau, Scott G.; Kozikowski, Alan P. [Journal of Medicinal Chemistry, 2009, vol. 52, # 21, p. 6757 - 6767]

11
[ 1176305-58-0 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
0.315 g	Stage #1: (S)-methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Stage #2: With ammonium hydroxide In water

Reference： [1]Location in patent: experimental part Ferraboschi, Patrizia; Mieri, Maria De; Galimberti, Fiorella [Tetrahedron Asymmetry, 2010, vol. 21, # 17, p. 2136 - 2141]

12
[ 1253091-76-7 ]
[ 141109-14-0 ]
[ 141109-16-2 ]

Yield	Reaction Conditions	Operation in experiment
	With protease from Bacillus licheniformis for 12h; aq. buffer; Resolution of racemate; optical yield given as %ee;

Reference： [1]Location in patent: scheme or table Ferraboschi, Patrizia; Mieri, Maria De; Galimberti, Fiorella [Tetrahedron Asymmetry, 2010, vol. 21, # 17, p. 2136 - 2141]

13
[ 141109-14-0 ]
[ 555-16-8 ]
C₁₆H₁₃ClN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-3,3'-bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 25℃; for 1h; Molecular sieve;

Reference： [1]Wang, Chao; Chen, Xiao-Hua; Zhou, Shi-Ming; Gong, Liu-Zhu [Chemical Communications, 2010, vol. 46, # 8, p. 1275 - 1277]

14
[ 141109-14-0 ]
[ 120202-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate / toluene / 25 - 30 °C 1.2: 85 - 90 °C 2.1: water / 25 - 35 °C 2.2: pH 7 - 8 3.1: sulfuric acid / acetone; methanol / 0 - 30 °C
	Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 27 h / 85 °C 1.2: 2 h / 20 °C 2.1: 4 h / 40 °C / Darkness 3.1: sulfuric acid / methanol / 25 °C
	Multi-step reaction with 3 steps 1.1: ammonium acetate / toluene / 40 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 25 °C 3.1: sulfuric acid / chloroform / 20 °C 3.2: 2 h / 10 °C

Multi-step reaction with 4 steps 1: 1,2-dichloro-ethane / 60 - 80 °C 2: potassium carbonate / acetonitrile / 70 - 80 °C 3: hydrogenchloride / water 4: water / 36 - 44 °C

Reference： [1]Current Patent Assignee: ORCHID PHARMA LTD - WO2011/12961, 2011, A1
[2]Current Patent Assignee: KANGYA OF NINGXIA PHARMACEUTICALS - CN103467486, 2016, B
[3]Current Patent Assignee: HENAN PURUI PHARMACEUTICAL TECHNOLOGY - CN104370935, 2017, B
[4]Current Patent Assignee: VALIANT CO., LTD. - CN112341475, 2021, A

15
[ 141109-14-0 ]
[ 113665-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / toluene / 25 - 30 °C 1.2: 85 - 90 °C 2.1: water / 25 - 35 °C 2.2: pH 7 - 8
	Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; potassium iodide / acetonitrile / 27 h / 85 °C 1.2: 2 h / 20 °C 2.1: 4 h / 40 °C / Darkness
	Multi-step reaction with 2 steps 1.1: potassium dihydrogen phosphate trihydrate / water / 15 h / 45 - 100 °C 1.2: 1 h / 0 - 3 °C / pH 1.2 - 1.5 2.1: methanol / 37 - 39 °C

Reference： [1]Current Patent Assignee: ORCHID PHARMA LTD - WO2011/12961, 2011, A1
[2]Current Patent Assignee: KANGYA OF NINGXIA PHARMACEUTICALS - CN103467486, 2016, B
[3]Current Patent Assignee: LANGFANG CITY ZEKANG MEDICINE TECH - CN111440139, 2020, A

16
[ 67-56-1 ]
[ 225918-58-1 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sulfuric acid at 0℃; for 5h; Reflux;

Reference： [1]Sashikanth, Suthrapu; Raju, Veeramalla; Somaiah, Sripathi; Rao, Peddisrinivasa; Reddy, Karnativenugopal [Synthesis, 2013, vol. 45, # 5, p. 621 - 624]

17
[ 89-98-5 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: methanol; water / 16 h / 25 - 30 °C 2: water; hydrogenchloride / diethyl ether / 4 h / 90 °C 3: sulfuric acid / 5 h / 0 °C / Reflux

Reference： [1]Sashikanth, Suthrapu; Raju, Veeramalla; Somaiah, Sripathi; Rao, Peddisrinivasa; Reddy, Karnativenugopal [Synthesis, 2013, vol. 45, # 5, p. 621 - 624]

18
[ 1430061-09-8 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: water; hydrogenchloride / diethyl ether / 4 h / 90 °C 2: sulfuric acid / 5 h / 0 °C / Reflux

Reference： [1]Sashikanth, Suthrapu; Raju, Veeramalla; Somaiah, Sripathi; Rao, Peddisrinivasa; Reddy, Karnativenugopal [Synthesis, 2013, vol. 45, # 5, p. 621 - 624]

19
[ 141109-14-0 ]
[ 114896-65-0 ]
[ 1314028-89-1 ]

Yield	Reaction Conditions	Operation in experiment
80.68%	With triethylamine In acetonitrile Reflux;

Reference： [1]Reddy, K. Tatendra; Kumar, K. Suneel; Omprakash; Dubey [Synthetic Communications, 2013, vol. 43, # 10, p. 1387 - 1396]

20
[ 141109-14-0 ]
[ 144750-52-7 ]

Reference： [1]Synthetic Communications,2013,vol. 43,p. 1387 - 1396

21
[ 141109-14-0 ]
[ 1396841-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / Reflux 2: hydrogenchloride / water / 25 - 55 °C

Reference： [1]Reddy, K. Tatendra; Kumar, K. Suneel; Omprakash; Dubey [Synthetic Communications, 2013, vol. 43, # 10, p. 1387 - 1396]

22
[ 141109-14-0 ]
[ 1396607-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / acetonitrile / Reflux 2: hydrogenchloride / water / 25 - 55 °C 3: hydrogenchloride / water; acetone / 25 °C

Reference： [1]Reddy, K. Tatendra; Kumar, K. Suneel; Omprakash; Dubey [Synthetic Communications, 2013, vol. 43, # 10, p. 1387 - 1396]

23
[ 141109-14-0 ]
[ 1422395-32-1 ]
[ 1422495-71-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogencarbonate In acetonitrile at 80℃; for 24h; Sealed tube;

Reference： [1]Zhu, Yaoqiu; Zhou, Jiang; Jiao, Bo [ACS Medicinal Chemistry Letters, 2013, vol. 4, # 3, p. 349 - 352]

24
2-(2-chlorophenyl)glycine methyl ester hydrochloride [ No CAS ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: methanol; acetonitrile; butanone / 11.5 h / Reflux 2: methanol / 0.5 h / Reflux
	Multi-step reaction with 2 steps 1: sulfuric acid / methanol; acetone / 20 h / 10 - 30 °C 2: ammonia / water; dichloromethane / 40 °C / pH 6.9 - 7.2

Reference： [1]Current Patent Assignee: KANGYA OF NINGXIA PHARMACEUTICALS - CN103467486, 2016, B
[2]Current Patent Assignee: LANGFANG CITY ZEKANG MEDICINE TECH - CN111440139, 2020, A

25
[ 147-71-7 ]
[ 141109-14-0 ]
[ 141109-15-1 ]

Yield	Reaction Conditions	Operation in experiment
83.7%	In methanol; acetonitrile; butanone; for 11.5h;Reflux;	In 1L eggplant bottle in turn by adding dextral tartaric acid 270g (1.8mol), methanol 360ml, stirring and heating completely dissolved, the preparation of tartaric acid methanol solution.(1.8 mol) of the light brown oil (Compound III) prepared above, 1800 ml of acetonitrile and 192.75 g (1.62 mol) of methyl ethyl ketone were added to a 5 L three-necked flask, and the mixture was heated to reflux and the above tartaric acid Methanol solution, about 1.5h drop is completed, return to the state continue to stir more than 10h, down to room temperature, filtration, cake 40 drying 5h, weighing 550g, yield 83.7%,

Reference： [1]Patent: CN103467486,2016,B .Location in patent: Paragraph 0090; 0091

26
2-amino-(2-chlorophenyl)ethanoic acid [ No CAS ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride / -10 - 35 °C 2: methanol; acetonitrile; butanone / 11.5 h / Reflux 3: methanol / 0.5 h / Reflux
	Multi-step reaction with 3 steps 1: sulfuric acid / 21 h / 35 - 65 °C 2: sulfuric acid / methanol; acetone / 20 h / 10 - 30 °C 3: ammonia / water; dichloromethane / 40 °C / pH 6.9 - 7.2

Reference： [1]Current Patent Assignee: KANGYA OF NINGXIA PHARMACEUTICALS - CN103467486, 2016, B
[2]Current Patent Assignee: LANGFANG CITY ZEKANG MEDICINE TECH - CN111440139, 2020, A

27
[ 141109-14-0 ]
[ 1198220-10-8 ]

Yield	Reaction Conditions	Operation in experiment
3 g	With ammonium hydroxide In methanol; water at 20℃; for 72h; Inert atmosphere;	29.2 Step 2. Into a 500 mE 24/40 joint single neck round bottomed flask equipped with a stir bar under nitrogen sparge was added a solution 5 grams of (S)-chlorophenylglycine methyl ester (0.025 mol) in 200 mE MeOH. Aqueous NH4OH (28-30% in water, 150 mE) was then added dropwise over approximately 20 minutes. The reaction was stirred 72 h under N2 atmosphere, and then concentrated under vacuum (.-5 -10 mm Hg) on a rotovap (l3uchi Rotovapor R-124, I3UCHI Eabortecimik AG, Switzerland). The residue was dissolved in water (250 mE), and extracted with CH2C12 (5x500 mE) using a separatory thnnel. The organic layers were combined into a 2 E Erlenmeyer flask, then dried (anhydrous Na2504), filtered to remove drying agent and concentrated via rotovap under vacuum (5-10mm Hg) to provide 3 grams of amide as a white solid.

Reference： [1]Current Patent Assignee: PROCTER & GAMBLE CO - US2017/57911, 2017, A1 Location in patent: Paragraph 0060; 0151; 0153

28
[ 67-56-1 ]
[ 141315-50-6 ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
5 g	With thionyl chloride In methanol at 20℃; for 24h; Reflux;	29.1 Step 1. In a 500 mE round-bottomed flask equipped with a reflux condenser capped with an addition funnel was added 5.0 g (S)-2-chlorophenylglycine (CAS 141315-50-6, 27.02 mol) and 200 mE MeOH. The solution was cooled to00 C. with an ice-water bath and thionyl chloride (CAS 7719-09-7, 25 mE) was added dropwise over 60 minutes. The reaction was warmed to RT for 24 hr. The solvents were stripped off on a rotary evaporator (Buchi Rotovapor R-124, I3UCHI Eabortechnik AG, Switzerland, 5-10 mm Hg) to provide an off-white solid. The solid was dissolved in CH2C12 (500 mE) and washed 3x200 mE sat NaHCO3 solution until the aqueous layer was basic (pH7-8) by pH papet The layers were separated and the organic layer was dried (Na2504) and then the drying agent was filtered off (l3uchner funnel). The mother liquor was concentrated under vacuum (5-10 mm Hg) using a rotary evaporator to provide the methyl ester as a white solid. 5 grams.

Reference： [1]Current Patent Assignee: PROCTER & GAMBLE CO - US2017/57911, 2017, A1 Location in patent: Paragraph 0060; 0151; 0152

29
[ 141109-14-0 ]
[ 1486-48-2 ]
methyl 2-(2-chlorophenyl)-2-(3,4,5-tris(benzyloxy)benzamido)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	Methyl 2-(2-chlorophenyl)-2-(3,4,5-tris(benzyloxy)benzamido)acetate (6h) To a CH2Cl2 solution (3 mL)of 3,4,5-tris(benzyloxy)benzoic acid (286 mg, 0.65 mmol), (S)-(+)-2-chlorophenylglycine methyl ester hydrochloride (130 mg, 0.65 mmol), EDCI (137 mg, 0.71 mmol), HOBt (50 mg, 0.33 mmol) and TEA(0.34 mL, 1.9 mmol) were added. After stirring overnight, the reaction mixture was diluted with ethylacetate and washed with water and brine, dried over MgSO4 and concentrated under reduced pressure.The residue was purified by flash column chromatography on silica gel (ethyl acetate/n-hexane = 1:3)to generate 30 mg of 6h (yield 8%). 1H-NMR (CDCl3) δ 7.46-7.26 (m, 18H), 7.13 (d, J = 6.9 Hz, 1H), 7.10(s, 2H), 6.01 (d, J = 7.0 Hz, 1H), 5.10 (d, J = 6.6 Hz, 4H), 5.09 (s, 2H), 3.77 (d, J = 8.4 Hz, 3H); 13C-NMR(CDCl3) δ 142.80, 138.02, 124.72, 113.56, 109.35, 108.60, 106.68, 105.53, 102.65, 102.19, 101.79, 100.75,100.56, 100.54, 100.18, 100.00, 99.94, 99.53, 99.30, 79.13, 47.12, 43.37, 27.29, 25.14; HRMS (EI) m/z calcd.for 621.1918; found 621.1917.

Reference： [1]Fei, Xiang; Je, In-Gyu; Shin, Tae-Yong; Kim, Sang-Hyun; Seo, Seung-Yong [Molecules, 2017, vol. 22, # 6]

30
[ 15022-15-8 ]
[ 141109-14-0 ]
C₁₅H₁₄ClNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.5%	With ammonium acetate In toluene at 40℃;	3 Weighed 2-thiophene acetaldehyde (12.6 g) And 20 g of S-o-chlorophenylglycine methyl ester, Was added to a 250 mL three-necked reaction flask, Add 100 mL of solvent to dichloromethane And the catalyst ammonium acetate 0.4g, Heated to reflux, the reaction temperature is 40 ° C, TLC trace monitoring, show the disappearance of raw materials, the reaction solution cooled to 30 ° C, add 100mL water, stirring and standing after the separation, the methylene chloride layer dried with anhydrous sodium sulfate. The filtrate was evaporated to dryness under reduced pressure to give a crude product of the solid imine intermediate which was recrystallized from ethanol to give 28.8 g of pure imine intermediate in a yield of 93.5%.

Reference： [1]Current Patent Assignee: HENAN PURUI PHARMACEUTICAL TECHNOLOGY - CN104370935, 2017, B Location in patent: Paragraph 0036; 0042; 0046-0048

31
[ 141109-14-0 ]
[ 141109-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonium acetate / toluene / 40 °C 2: sodium tetrahydroborate / tetrahydrofuran / 25 °C
	Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 60 - 80 °C 2: potassium carbonate / acetonitrile / 70 - 80 °C

Reference： [1]Current Patent Assignee: HENAN PURUI PHARMACEUTICAL TECHNOLOGY - CN104370935, 2017, B
[2]Current Patent Assignee: VALIANT CO., LTD. - CN112341475, 2021, A

32
[ 141109-14-0 ]
[ 213018-92-9 ]

Yield	Reaction Conditions	Operation in experiment
88.9%	With hydrogenchloride at 0 - 5℃;	1.2; 2.2 Example 1: 2) 200mL methanol and 50mL concentrated sulfuric acid was added to the reaction flask, stir, then add Intermediate 3(40g, 0.08mol), heated to reflux for 10 hours, distilled,The residue was added ethyl acetate 200mL and 40mL, extracted, the organic layer was washed with saturated sodium bicarbonate to pH8-9,Dried over anhydrous sodium sulfate, filtered, and the filtrate was cooled to 0-5 ° C, hydrogen chloride gas was introduced,Ventilation end, standing crystallization, filtration, drying too(S) -chlorophenglycine methyl ester hydrochloride (16.8 g, yield 88.9%).

Reference： [1]Current Patent Assignee: HENAN PURUI MEDICINE TECH - CN106748853, 2017, A Location in patent: Paragraph 0005; 0006; 0007; 0008

33
[ 141109-14-0 ]
C₂₅H₂₂ClF₆N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sulfuric acid / toluene / 1 h / 70 - 80 °C 2: methanesulfonic acid; sodium tetrahydroborate / toluene; isopropyl alcohol; 1,2-dimethoxyethane / 4 h / -65 - -55 °C

Reference： [1]Current Patent Assignee: THE KALYANI GROUP - WO2019/186260, 2019, A1

34
[ 141109-14-0 ]
[ 764667-65-4 ]
C₂₅H₂₀ClF₆N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In toluene; at 70 - 80℃; for 1h;	To a stirred solution of compound II (50. Og, 0.123 moles) and compound III (34.4g, 0.172 moles), toluene (750mL, 15V), cone sulfuric acid (l.l76g, 0.0123 moles) was added and heated the reaction mixture to 70C to 80C for lh. The solvent was removed by distillation from reaction mixture under reduced pressure till minimum stirrable volume. To above reaction mixture fresh toluene (750mL, 15V) was charged and continued distillation of solvent below 80C. After completion of reaction, the reaction mixture was allowed to cool to 25C to 30C. The reaction mixture was quenched by water (300mL), stirred for 30 min. and the aqueous and organic layer were separated. The organic layer was washed with 2N hydrochloric acid (300mL), saturated sodium bicarbonate solution (300mL) and evaporated under reduced pressure to yield crude compound IV as a yellow to brown solid (72g, 99%) with chiral HPLC purity 97.77%, MS: 588 [M+H]+, 1H NMR: (DMSO, 400 MHz): 3.55-3.60 (3H, s); 3.55-3.60 (2H, s); 3.85-3.98 (2H, bt); 4.12-4.18 (2H, bt); 4.90 (2H, s); 5.13 (1H, s); 5.60-5.62 (1H, d), 7.14-7.54 (6 H, m); 10.42-10.44 (1H, s).

Reference： [1]Patent: WO2019/186260,2019,A1 .Location in patent: Page/Page column 13

35
[ 141109-14-0 ]
C₉H₈ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	General procedure for the preparation of the isolated azide compounds. General procedure: To a 50-ml glass round-bottom flask was added sequentially the primary amine 2 (1.0 mmol; aliphatic, aromatic or heteroaromatic; as free naked amine or as HCl, MsOH, TsOH or tartrate salt), FSO2N3 solution (containing 1.0 mmol FSO2N3, approximately 200 mM in DMF/MTBE 1:1, v/v, approximately 5 ml, volume adjusted according to the concentration; prepared according to the above procedure and diluted with equal volume of DMF) and aqueous KHCO3 solution (3.0 M, 1.33 ml, containing 4.0 mmol KHCO3). The reaction mixture was stirred for 5 min at room temperature, while monitoring by LC-MS. After completion, EtOAc (40 ml) was added and the mixture was washed sequentially with brine (60 ml × 6), water (60 ml × 2) and brine (60 ml), dried over Na2SO4, concentrated by rotary evaporation and dried under vacuum to afford the azide product 3. For products containing acidic functional groups, this extraction process was modified with acidified aqueous phase (acidified with aqueous HCl). Detailed procedures and the various modifications, as well as the characterization data for each compound, can be found in Supplementary Information 1.

Reference： [1]Meng, Genyi; Guo, Taijie; Ma, Tiancheng; Zhang, Jiong; Shen, Yucheng; Sharpless, Karl Barry; Dong, Jiajia [Nature, 2019, vol. 574, # 7776, p. 86 - 89]

36
(+)-2-chlorophenylglycine methyl ester tartrate [ No CAS ]
[ 141109-14-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In dichloromethane; water	1-2 Add 300ml of dichloromethane, 160ml of water, and 80g of sodium carbonate to the three-necked flask.Then add 140g of (+) 2-chlorophenylglycine methyl ester tartrate,After the reaction was completed, the liquids were separated, the aqueous layer was extracted three times with 50 ml of dichloromethane, the organic layers were combined, dried over anhydrous sodium sulfate, centrifuged, and the filtrate was taken to recover the dichloromethane under reduced pressure to obtain (+) o-chlorophenylglycine methyl ester.

Reference： [1]Current Patent Assignee: HUNAN DINUO PHARMACEUTICAL BY SHARE - CN110776519, 2020, A Location in patent: Paragraph 0034; 0054; 0070

37
[ 40412-06-4 ]
[ 141109-14-0 ]
(+) α-(2-thiopheneethylamino)-α-(2-chlorophenyl)acetate methyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate With dipotassium hydrogenphosphate In acetonitrile at 20℃; for 1h; Stage #2: 2-(2-thienyl)ethyl tosylate In acetonitrile at 48℃;	1-2 Add 600ml acetonitrile and 140g dipotassium hydrogen phosphate into a three-necked flask,Mix with (+) o-chlorophenylglycine methyl ester obtained in the previous step, and stir at 20°C for 1 hour. Then add 170g of 2-(2-thienyl)ethanol p-toluenesulfonate, and then increase the temperature to 48°C to keep the reaction temperature. After the reaction, centrifuge, collect the mother liquor into the reaction vessel, add appropriate amount of hydrochloric acid to pH 4 while stirring, stir for 4 hours, centrifuge, and dry the obtained solid at 50°C to obtain (+) α-(2-thiopheneethylamino) )-α-(2-Chlorophenyl)acetate methyl ester hydrochloride.

Reference： [1]Current Patent Assignee: HUNAN DINUO PHARMACEUTICAL BY SHARE - CN110776519, 2020, A Location in patent: Paragraph 0036; 0054-0055; 0070-0071

38
[ 141109-14-0 ]
clopidogrel sulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium dihydrogen phosphate trihydrate / water / 15 h / 45 - 100 °C 1.2: 1 h / 0 - 3 °C / pH 1.2 - 1.5 2.1: methanol / 37 - 39 °C 3.1: chlorosulfonic acid / 1,2-dichloro-ethane / 4 h / 20 °C

Reference： [1]Current Patent Assignee: LANGFANG CITY ZEKANG MEDICINE TECH - CN111440139, 2020, A

39
[ 67-56-1 ]
C₂₀H₁₆ClN₂OP [ No CAS ]
[ 141109-14-0 ]
[ 141109-16-2 ]

Yield	Reaction Conditions	Operation in experiment
64 % ee	Stage #1: methanol; C₂₀H₁₆ClN₂OP With hydrogenchloride at 80℃; for 15h; Stage #2: With sodium carbonate In water Overall yield = 54 percent; enantioselective reaction;

Reference： [1]Junge, Thorsten; Titze, Marvin; Frey, Wolfgang; Peters, René [ChemCatChem, 2021, vol. 13, # 6, p. 1509 - 1512]

40
[ 141109-14-0 ]
(S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1,2-dichloro-ethane / 60 - 80 °C 2: potassium carbonate / acetonitrile / 70 - 80 °C 3: hydrogenchloride / water

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN112341475, 2021, A

41
[ 141109-14-0 ]
[ 999-97-3 ]
C₁₂H₁₈ClNO₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In 1,2-dichloro-ethane at 60 - 80℃;	1.1; 2.1; 3.1 (1) Synthesis of (S)-o-chlorophenylglycine methyl ester protected by trimethylsilyl group Add 56.1g (0.3477mol) 1,1,1,3,3,3-hexamethyldiazosilane (referred to as HMDS) in the reactor,138.4g(0.6954moL)(S)-o-chlorophenylglycine methyl ester,348.9g dichloroethane,Heat to 6080,Insulation reaction 8h16h,After the reaction is complete,Steam out HMDS under reduced pressure (6080, -0.06MPa-0.1MPa),Obtain 200.1g of light yellow liquid (theoretical yield 200.2g),The yield is 100.0%,The GC purity is 94.0%.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN112341475, 2021, A Location in patent: Paragraph 0075-0077; 0082-0084; 0089-0091

42
[ 865187-81-1 ]
[ 141109-14-0 ]
[ 113665-84-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Bis(p-nitrophenyl) phosphate In toluene at 100℃; for 36h; Sealed tube; Molecular sieve; Green chemistry;	Amine 11 (399.3 mg, 2.0 mmol, 1.0 eq.), diol 14 (379.7 mg, 2.4 mmol, 1.0eq.), were added to a sealed tube, 5.0 mL of toluene was added and stirred. Then [Ir] catalyst 15 (79.7 mg, 0.1 mmol, 0.05eq.) and phosphoric acid 16 (68.1 mg, 0.2 mmol, 0.1eq.), 4 molecular sieve (500.1 mg) was added, heated at 100 C for 36h. The reaction mass was allowed to cool to rt, then washed with 5% NaHCO3 solution, water, evaporated under vacuum. The crude mass was purified by silica gel column chromatography, eluted with 5% ethyl acetate in n-hexane to give clopidogrel (4) as a yellow oil.

Reference： [1]Swain, Sharada Prasanna; Shri, Om; Ravichandiran [Molecular catalysis, 2021, vol. 508]

43
[ 71637-34-8 ]
[ 141109-14-0 ]
C₁₄H₁₄ClNO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Bis(p-nitrophenyl) phosphate In toluene at 100℃; for 24h; Green chemistry;

Reference： [1]Swain, Sharada Prasanna; Shri, Om; Ravichandiran [Molecular catalysis, 2021, vol. 508]

44
[ 5402-55-1 ]
[ 141109-14-0 ]
[ 141109-20-8 ]

Yield	Reaction Conditions	Operation in experiment
	With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Bis(p-nitrophenyl) phosphate In toluene at 100℃; for 24h; Green chemistry;

Reference： [1]Swain, Sharada Prasanna; Shri, Om; Ravichandiran [Molecular catalysis, 2021, vol. 508]

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H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 141109-14-0 ] {[proInfo.proName]}

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[ 141109-14-0 ] Synthesis Path-Upstream 1~1

[ 141109-14-0 ] Synthesis Path-Downstream 1~44

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Aryls

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Amines

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[ 141109-14-0 ]