141109-20-8

Basic information

• Product Name: (+)-(S)-Methyl alpha-[[2-(2-thienyl)ethyl]amino]-alpha-(2-chlorophenyl)acetate
• Synonyms: (as)-2-chloro-alpha-[[2-(2-thienyl)ethyl]amino]-benzeneacetic acid methyl ester;(+)-(S)-Methyl alpha-[[2-(2-thienyl)ethyl]amino]-alpha-(2-chlorophenyl)acetate;S-(+)-METHYL 2-(2-CHLOROPHENYL)-2-(2-(THIOPHEN-2-YL);Clopidogrel Thienylethyl IMpurity;Clopidogrel IMpurity;(S)-Methyl 2-(2-chlorophenyl)-2-((2-(thiophen-2-yl)ethyl)aMino)acetate;methyl (2S)-2-(2-chlorophenyl)-2-(2-thiophen-2-ylethylamino)acetate
• CAS NO: 141109-20-8
• Molecular Formula: C₁₅H₁₆ClNO₂S
• Molecular Weight: 309.81
• Mol File: 141109-20-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 416.596 °C at 760 mmHg
• Flash Point: 205.75 °C
• Appearance: /
• Density: 1.254
• Vapor Pressure: 3.78E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 5.11±0.29(Predicted)
• CAS DataBase Reference: (+)-(S)-Methyl alpha-[[2-(2-thienyl)ethyl]amino]-alpha-(2-chlorophenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-Methyl alpha-[[2-(2-thienyl)ethyl]amino]-alpha-(2-chlorophenyl)acetate(141109-20-8)
• EPA Substance Registry System: (+)-(S)-Methyl alpha-[[2-(2-thienyl)ethyl]amino]-alpha-(2-chlorophenyl)acetate(141109-20-8)

Safety Data

• Hazardous Substances Data: 141109-20-8(Hazardous Substances Data)

Usage

General Description

(+)-(S)-Methyl alpha-[[2-(2-thienyl)ethyl]amino]-alpha-(2-chlorophenyl)acetate, also known as eslicarbazepine acetate, is a chemical compound used as an anticonvulsant medication. It is a prodrug of eslicarbazepine, which is used in the treatment of epilepsy. Eslicarbazepine acetate works by stabilizing the inactive state of sodium channels in the brain, which helps to prevent the uncontrolled electrical activity that can lead to seizures. It is typically taken orally and is absorbed into the bloodstream where it is metabolized into eslicarbazepine, the active form of the drug. Eslicarbazepine acetate is approved for use in the United States and Europe for the treatment of partial-onset seizures in adults.

InChI:InChI=1/C15H16ClNO2S.H2O4S/c1-19-15(18)14(12-6-2-3-7-13(12)16)17-9-8-11-5-4-10-20-11;1-5(2,3)4/h2-7,10,14,17H,8-9H2,1H3;(H2,1,2,3,4)

Upstream product

• 40412-06-4 2-(2-thienyl)ethyl tosylate 
• 141109-14-0 methyl (S)-(+)-2-amino-2-(2-chlorophenyl)acetate 
• 213018-92-9 (S)-methyl 2-amino-2-(2-chlorophenyl)acetate hydrochloride salt 
• 15022-15-8 2-thienylacetaldehyde 
• 30433-91-1 [2-(2-thyenyl)ethyl]amine 
• 34966-49-9 methyl 2-chlorobenzoylformate 
• 26478-16-0 2-(2-Bromoethyl)thiophene 
• 5402-55-1 2-thiophenethanol 

Downstream Products

• 113665-84-2 (S)-(+)-clopidogrel 
• 120202-66-6 (S)-(+)-clopidogrel bisulfate 
• 141109-18-4 (S)-(+)-α-(2-thienylethylamino)-α-(2-chlorophenyl)acetic acid methyl ester hydrochloride 

Relevant articles and documents

Iridium and bis(4-nitrophenyl)phosphoric acid catalysed amination of diol by hydrogen-borrowing methodology for the synthesis of cyclic amine: Synthesis of clopidogrel

The borrowing hydrogen method is an environmentally benign process for the synthesis of amines, as H2O is the side product. A new green process for the amination of diol by [Ir] catalyst 15 and bis(4-nitrophenyl)phosphoric acid for the synthesis of cyclic amine is reported. This method was successfully applied for the synthesis of antiplatelet drug clopidogrel.

Synthetic hydrosulfuric acid clopidogrel and intermediate of the new method (by machine translation)

The invention relates to a synthesis of the clopidogrel hydrogen sulfate of the new method, through 2 - thiophene ethylamine and N - benzyl - 2 - (2 - chlorophenyl) - 2 - carbonyl acetamide generate condensation reaction, generating imine; imine asymmetric hydrogenation reaction is reduced to the corresponding secondary amine. Under acidic conditions, secondary amine with formaldehyde generating ring, get the clopidogrel free base, then acidified by sulfuric acid, to obtain the clopidogrel hydrogen sulfate. The present invention provides a synthetic route of the short, relates to the reaction are classical organic chemical reaction, mild reaction conditions, the operation is simple, with high enantio-selectivity, high yield, high turn over number of characteristics, the vast majority of the substrate in the thousandths of a dosage of the catalyst obtained in the circumstances of 99% or more of the conversion and 97% -99% ee value of, to achieve the highest transformed number 100000, has extremely high industrial application value. (by machine translation)

Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel

The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation.