141109-14-0

Basic information

• Product Name: (S)-(+)-2-Chlorophenylglycine methyl ester
• Synonyms: of (S)-(+)-2-Chlorophenylglycine Methyl ester tartaric acid;L (+)-2-Chlorophenyl Glycine Methyl Ester Tartarate;(S)-(+)-2-chlorophenyl glycine methyl ester tartrate salt;D-o-chlorophenyl glycine methyl ester tartrate;(S)-Methyl 2-amino-2-(2-chlorophenyl)acetate tartaric salt;(alphaS)-alpha-Amino-2-chlorophenyl-acetic acid methyl ester;s(+) - 2- Chlorophenylglycine methylester tarterate
• CAS NO: 141109-14-0
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• EINECS: 1308068-626-2
• Product Categories: INTERMEDIATES OF CLOPIDOGREL;chiral
• Mol File: 141109-14-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 270.1 °C at 760 mmHg
• Flash Point: 117.2 °C
• Appearance: light yellow to yellow liquid
• Density: 1.258 g/cm³
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.15±0.10(Predicted)
• CAS DataBase Reference: (S)-(+)-2-Chlorophenylglycine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-Chlorophenylglycine methyl ester(141109-14-0)
• EPA Substance Registry System: (S)-(+)-2-Chlorophenylglycine methyl ester(141109-14-0)

Safety Data

• Hazardous Substances Data: 141109-14-0(Hazardous Substances Data)

Usage

Uses

(S)-(+)-2-Chlorophenylglycine methyl ester tartrate

InChI:InChI=1/C9H10ClNO2.ClH/c1-13-9(12)6-11-8-5-3-2-4-7(8)10;/h2-5,11H,6H2,1H3;1H

Synthetic route

2-chlorophenylglycine methyl ester L-(+)-tartaric acid (141109-15-1) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
In methanol for 0.5h; Reflux;	95%
With ammonia In dichloromethane; water at 40℃; pH=6.9 - 7.2;	70%
With ammonia In dichloromethane; water for 0.5h; pH=7.0 - 7.2;
With sodium hydroxide In water; toluene at 0 - 10℃; pH=9;

methanol (67-56-1) + (S)-2-(2-chlorophenyl)glycinamide hydrochloride (1198213-98-7) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
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	94%

methanol (67-56-1) + (2S)-2-(2-chlorophenyl)glycine hydrochloride (225918-58-1) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
With sulfuric acid at 0℃; for 5h; Reflux;	85%

L-(+)-tartaric acid salt of α-amino-(2-chlorophenyl)acetic acid methyl ester → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
With sodium hydrogencarbonate In dichloromethane; water at 5℃; for 1.66667h; pH=7.46;

(S)-methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate (1176305-58-0) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
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 pH=7;	0.315 g

methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate (1253091-76-7) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + α-amino-(2-chlorophenyl)acetic acid methyl ester (141109-16-2)

Conditions	Yield
With protease from Bacillus licheniformis for 12h; pH=7.5; aq. buffer; Resolution of racemate; optical yield given as %ee;

2-chloro-benzaldehyde (89-98-5) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
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 View Scheme

(2S)-(2-chlorophenyl){[(1S)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydrochloride (1430061-09-8) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

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

2-(2-chlorophenyl)glycine methyl ester hydrochloride (141109-14-0, 141109-16-2, 141109-13-9) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; acetonitrile; butanone / 11.5 h / Reflux 2: methanol / 0.5 h / Reflux View Scheme
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 View Scheme

2-amino-(2-chlorophenyl)ethanoic acid (86169-24-6, 141196-64-7, 141315-50-6, 88744-36-9) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
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 View Scheme
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 View Scheme

methanol (67-56-1) + (S)-2-amino-(2-chlorophenyl)ethanoic acid (141315-50-6) → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
With thionyl chloride In methanol at 20℃; under 760.051 Torr; for 24h; Reflux;	5 g

(+)-2-chlorophenylglycine methyl ester tartrate → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0)

Conditions	Yield
With sodium carbonate In dichloromethane; water

methanol (67-56-1) + C20H16ClN2OP → methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + α-amino-(2-chlorophenyl)acetic acid methyl ester (141109-16-2)

Conditions	Yield
Stage #1: methanol; C20H16ClN2OP With hydrogenchloride at 80℃; for 15h; Stage #2: With sodium carbonate In water Overall yield = 54 percent; enantioselective reaction;	A n/a B n/a

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C12H18ClNO2Si

Conditions	Yield
In 1,2-dichloro-ethane at 60 - 80℃;	100%

2-thienylacetaldehyde (15022-15-8) + methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → C15H14ClNO2S

Conditions	Yield
With ammonium acetate In toluene at 40℃; Solvent; Temperature; Reagent/catalyst;	93.5%

2-(2-thienyl)ethyl tosylate (40412-06-4) + methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride

Conditions	Yield
Stage #1: 2-(2-thienyl)ethyl tosylate; methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate With sodium hydrogencarbonate; potassium iodide In acetonitrile at 85℃; for 27h; Stage #2: With hydrogenchloride In water at 20℃; for 2h;	91%
Stage #1: 2-(2-thienyl)ethyl tosylate; methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate With potassium dihydrogen phosphate trihydrate In water at 45 - 100℃; for 15h; Stage #2: With hydrogenchloride at 0 - 3℃; for 1h; pH=1.2 - 1.5;	89%
Stage #1: 2-(2-thienyl)ethyl tosylate; methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate With dipotassium hydrogenphosphate In acetic acid tert-butyl ester at 92.5℃; for 30h; Stage #2: With hydrogenchloride In water; ethyl acetate at 12.5℃; for 0.416667h; Product distribution / selectivity;	66.3%

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-methyl 2-amino-2-(2-chlorophenyl)acetate hydrochloride salt (213018-92-9)

Conditions	Yield
With hydrogenchloride at 0 - 5℃;	88.9%

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → C9H8ClN3O2

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	83%

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + 3-(2'-iodoethyl) thiophene (114896-65-0) → methyl (S)-(+)-2-(2-(thiophen-3-yl)ethylamino)-2-(2-chlorophenyl)acetate (1314028-89-1)

Conditions	Yield
With triethylamine In acetonitrile Reflux;	80.68%

2-(3-hydroxymethylthiophen-2-yl)ethanol (865187-81-1) + methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-(+)-clopidogrel (113665-84-2)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; Bis(p-nitrophenyl) phosphate In toluene at 100℃; for 36h; Solvent; Time; Temperature; Sealed tube; Molecular sieve; Green chemistry;	80%

2-(2-thienyl)ethyl tosylate (40412-06-4) + methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate (141109-20-8)

Conditions	Yield
With sodium hydrogencarbonate; potassium iodide In acetonitrile for 12h; Reflux;	70%
With triethylamine at 78 - 82℃; for 8 - 10h; Product distribution / selectivity;

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + 5-(2-methylbenzothiazol-5-yloxymethyl)isoxazole-3-carboxylic acid (1193342-88-9) → (2-chlorophenyl){[5-(2-methylbenzothiazol-5-yloxymethyl)isoxazole-3-carbonyl]-(S)-amino}acetic acid methyl ester (1193343-40-6)

Conditions	Yield
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	59.4%

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + 3,4,5-tribenzyloxybenzoic acid (1486-48-2) → methyl 2-(2-chlorophenyl)-2-(3,4,5-tris(benzyloxy)benzamido)acetate

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide	8%

2-(2-bromoethyl)-3-(bromomethyl)thiophene (865187-82-2) + methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-(+)-clopidogrel (113665-84-2)

Conditions	Yield
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;

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + 4-nitrobenzaldehdye (555-16-8) → C16H13ClN2O4

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

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-(+)-clopidogrel bisulfate (120202-66-6)

Conditions	Yield
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 View Scheme
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 View Scheme
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 View Scheme
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 View Scheme

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-(+)-clopidogrel (113665-84-2)

Conditions	Yield
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 View Scheme
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 View Scheme
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 View Scheme

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → methyl (S)-(+)-2-(2-chlorophenyl)-2-(4,5-dihydrothieno[2,3-c]pyridin-6(7H)-yl)acetate (1396841-05-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / Reflux 2: hydrogenchloride / water / 25 - 55 °C View Scheme

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → methyl (S)-(+)-2-(2-chlorophenyl)-2-(4,5-dihydrothieno[2,3-c]pyridine-6(7H)-yl)acetate hydrochloride (1396607-35-4)

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

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) + 1,1,2,2-tetradeutero-2-(thiophen-2-yl)ethyl 4-methylbenzenesulfonate (1422395-32-1) → (S)-methyl 2-(2-chlorophenyl)-2-(1,1,2,2-tetradeutero-2-(thiophen-2-yl)ethylamino)acetate (1422495-71-3)

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

methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate (141109-14-0) → (S)-2-amino-2-(2-chlorophenyl) acetamide (1198220-10-8)

Conditions	Yield
With ammonium hydroxide In methanol; water at 20℃; under 760.051 Torr; for 72h; Inert atmosphere;	3 g

Upstream product

• 67-56-1 methanol 
• 141315-50-6 (S)-2-amino-(2-chlorophenyl)ethanoic acid 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 
• 141109-14-0 2-(2-chlorophenyl)glycine methyl ester hydrochloride 
• 1430061-09-8 (2S)-(2-chlorophenyl){[(1S)-1-(4-methoxyphenyl)ethyl]amino}acetonitrile hydrochloride 
• 89-98-5 2-chloro-benzaldehyde 
• 225918-58-1 (2S)-2-(2-chlorophenyl)glycine hydrochloride 
• 1253091-76-7 methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 
• 1176305-58-0 (S)-methyl 2-((tert-butoxycarbonyl)amino)-2-(2-chlorophenyl)acetate 
• 1198213-98-7 (S)-2-(2-chlorophenyl)glycinamide hydrochloride 
• 141109-15-1 2-chlorophenylglycine methyl ester L-(+)-tartaric acid 
• 1233361-76-6 L-(+)-tartaric acid salt of α-amino-(2-chlorophenyl)acetic acid methyl ester 

Downstream Products

• 92233-02-8 (Ethoxycarbonyl)-4 (o-chlorophenyl)-2 methyl-3 aza-3 butanoate de methyle 
• 113665-84-2 (S)-(+)-clopidogrel 
• 1322877-80-4 trimethyl (2S,3S,4R,5S)-2-(2-chlorophenyl)-5-(4-nitrophenyl)pyrrolidine-2,3,4-tricarboxylate 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 141109-18-4 (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride 
• 141109-15-1 2-chlorophenylglycine methyl ester L-(+)-tartaric acid 
• 1198220-10-8 (S)-2-amino-2-(2-chlorophenyl) acetamide 
• 141109-16-2 α-amino-(2-chlorophenyl)acetic acid methyl ester 
• 141109-20-8 methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate 
• 213018-92-9 (S)-methyl 2-amino-2-(2-chlorophenyl)acetate hydrochloride salt 
• 1422495-71-3 (S)-methyl 2-(2-chlorophenyl)-2-(1,1,2,2-tetradeutero-2-(thiophen-2-yl)ethylamino)acetate 
• 1423136-84-8 methyl 4-benzoyl-2-(2-chlorophenyl)-5-(4-nitrophenyl)-2,5-dihydro-1H-pyrrole-2-carboxylate 
• 1423136-85-9 methyl 4-benzoyl-2-(2-chlorophenyl)-5-(4-nitrophenyl)-2,5-dihydro-1H-pyrrole-2-carboxylate 
• 138228-59-8 (R)-2-(benzylideneamino)-2-(2-chlorophenyl)acetamide 

Relevant articles and documents

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