94188-84-8

Basic information

• Product Name: methyl 2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate
• Synonyms: methyl 2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate;Clopidogrelum;Clopidogrelum [latin];Methyl 2-(2-chlorophenyl)-2-(4,5,6,7-tetrahydrothieno(3,2-C)pyridin-5-yl)acetate;Pcr 4099;Thieno(3,2-C)pyridine-5(4H)-acetic acid, alpha-(2-chlorophenyl)-6,7-dihydro-, methyl ester
• CAS NO: 94188-84-8
• Molecular Formula: C16H16ClNO2S
• Molecular Weight: 321.82174
• Mol File: 94188-84-8.mol
• Article Data: 113

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl 2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate(94188-84-8)
• EPA Substance Registry System: methyl 2-(2-chlorophenyl)-2-(9-thia-4-azabicyclo[4.3.0]nona-7,10-dien-4-yl)acetate(94188-84-8)

Safety Data

• Hazardous Substances Data: 94188-84-8(Hazardous Substances Data)

Upstream product

• 141109-20-8 methyl (S)-2-(2-chlorophenyl)-2-[2-(thien-2-yl)ethylamino]acetate 
• 50-00-0 formaldehyd 
• 144457-28-3 SR 26334 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 144750-42-5 (S)-(+)-2-(2-chlorophenyl)-2-(6,7-dihydrothieno-[3,2-c]pyridin-5(4H)-yl)acetic acid hydrochloride 
• 141109-18-4 (+)-α-[(2-thien-2-yl)-ethylamino]-α-(2-chlorophenyl)methylacetate hydrochloride 
• 855522-39-3 (αS,7RS)-methyl-α-(7-hydroxy-4,5,6,7-tetrahydro-5-thieno[3,2-c]pyridyl)-o-chlorophenylacetate bisulfate 
• 855522-40-6 (αS,7RS)-methyl-α-(7-hydroxy-4,5,6,7-tetrahydro-5-thieno[3,2-c]pyridyl)-o-chlorophenylacetate hydrochloride 
• 855522-41-7 (αS,7RS)-methyl-α-(7-hydroxy-4,5,6,7-tetrahydro-5-thieno[3,2-c]pyridyl)-o-chlorophenylacetate para-toluenesulfonate 
• 444728-13-6 (+)-α-(4,5,6,7-tetrahydrothieno[3,2-c]-5-pyridyl)-α-2-chlorophenylacetamide 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 40412-06-4 2-(2-thienyl)ethyl tosylate 

Downstream Products

• 1093351-62-2 C₁₆H₁₄⁽²⁾H₂ClNO₂S 
• 144457-28-3 SR 26334 
• 767612-34-0 R-361015 
• 1351983-68-0 C₁₆H₁₈ClNO₄S 

Relevant articles and documents

Copper (II) bromide catalysed one pot bromination and amination for the green, cost-effective synthesis of clopidogrel

Copper (II) bromide catalyzed one pot α-bromination and followed by amination of a benzylic ester is reported. The α-bromination of ester by copper (II) bromide generates copper (I) bromide and HBr. The copper (I) bromide is oxidized to copper (II) bromide by N-Methylmorpholine-N-Oxide (NMO) in presence of HBr. The amines undergo nucleophilic substitution reaction with α-brominated ester compound. This methodology was applied for the synthesis of the familiar antiplatelet drug clopidogrel. This green process is an alternate to classical methods for the synthesis of clopidogrel, which requires, generates stochiometric amount of brominating agents and HBr, respectively.

Method for recycling S - O-chloromandelic acid

The invention belongs to the technical field of chemical synthesis, and discloses a method for recycling S-o-chloromandelic acid. The o-chloromandelic acid is a clopidogrel hydrogen sulfate starting material. The method is characterized by comprising the following steps: concentrating a lipid solution of S-o-chloromandelic acid to dryness, and adding an alkaline aqueous solution to react at a hightemperature to racemize the S-o-chloromandelic acid; after the reaction is completed, adding a C2-C8 lipid solvent and adjusting the pH of the solution with an inorganic acid to be acidic; separatingan aqueous phase from an organic phase, and allowing the organic phase to be dried and directly reacted with a resolving agent to prepare R-o-chloromandelic acid. The invention provides a method forrecycling clopidogrel hydrogen sulfate intermediate waste, the influence of reaction byproducts on the environment is eliminated, the S-o-chloromandelic acid is converted and then used in the preparation process of clopidogrel hydrogen sulfate, and the economic value is very high.

Preparation method of sulfonic clopidogrel impurity

The invention discloses a preparation method of a sulfonic clopidogrel impurity. The preparation method comprises the following steps: reacting thiophene-2-ethanol with toluenesulfonyl chloride to generate p-toluenesulfonic acid-2-thienylethyl ester; carrying out esterification on o-chlorophenylglycine and methanol to generate o-chlorophenylglycine methyl ester; resolving the o-chlorophenylglycinemethyl ester by using L(+) tartaric acid; converting into free S-(+)-o-chlorophenylglycine methyl ester in dichloromethane; carrying out a condensation reaction on the p-toluenesulfonic acid-2-thienylethyl ester and the S-(+)-o-chlorophenylglycine methyl ester under an alkaline condition; acidifying the obtained product to generate (S)-2-(2-thienylethylamino)(2-chlorphenyl)methyl acetate, carrying out a condensation reaction on the (S)-2-(2-thienylethylamino)(2-chlorphenyl)methyl acetate and formaldehyde to obtain clopidogrel, and carrying out a reaction on the clopidogrel and chlorosulfonicacid to generate sulfonic clopidogrel impurity. The preparation method of the sulfonic clopidogrel impurity has the advantages of mild reaction conditions, accessible raw materials, low cost and highyield and purity.