(2S)-Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

Base Information

• Chemical Name: (2S)-Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate
• CAS No.: 1147350-75-1
• Molecular Formula: C16H16ClNO3S
• Molecular Weight: 337.827
• Hs Code.: 2934999090
• Mol file: 1147350-75-1.mol

Synonyms:(2S)-Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate;Clopidogrel thiolactone

Chemical Property of (2S)-Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

Chemical Property:

• Boiling Point: 488.1±45.0 °C(Predicted)
• PKA: 3.41±0.20(Predicted)
• PSA: 71.91000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 2.76610

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Clopidogrelthiolactone >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl (αS)-α-(2-chlorophenyl)-2,6,7,7a-tetrahydro-2-oxothieno[3,2-c]pyridine-5(4H)-acetate is the essential intermediate metabolite from which the active metabolite of Clopidogel is formed.

Technology Process of (2S)-Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate

There total 9 articles about (2S)-Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

(R)-2-(2-chlorophenyl)-2-(4-nitrobenzenesulfonyloxy)acetic acid methyl ester + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → 2-Oxoclopidogrel (1147350-75-1,109904-27-0)

Guidance literature:

With potassium hydrogencarbonate; In acetonitrile; at 20 ℃; for 26h; Inert atmosphere;

DOI:10.1021/jm300038c

Reference yield:

(R)-2-(2-chlorophenyl)-2-(4-nitrobenzenesulfonyloxy)acetic acid methyl ester + 5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride (109904-37-2) → 2-Oxoclopidogrel (1147350-75-1,109904-27-0)

Guidance literature:

5,6,7,7a-tetrahydrothieno[3,2-c]pyridine-2(4H)-one monohydrochloride; With potassium carbonate; In dichloromethane; water; for 0.166667h;

(R)-2-(2-chlorophenyl)-2-(4-nitrobenzenesulfonyloxy)acetic acid methyl ester; In dichloromethane; for 1h; Reflux;

Reference yield:

methyl (R)-2-chloromandelate (32345-59-8) → 2-Oxoclopidogrel (1147350-75-1,109904-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 3 h / 0 °C

2.1: potassium carbonate / dichloromethane; water / 0.17 h

2.2: 1 h / Reflux

With dmap; potassium carbonate; triethylamine; In dichloromethane; water;

upstream raw materials:

(S)-(+)-clopidogrel

(R)-2-chloromandelic acid

methyl (R)-2-chloromandelate

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride

Downstream raw materials:

cis-5-thiol metabolite

methyl (S,E)-2-(2-chlorophenyl)-2-(2-acetoxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate monohydrochloride

Refernces

• 1、 Nishihara, Mitsuhiro,Yamasaki, Hitomi,Czerniak, Richard,Jenkins, Helen. "In Vitro Assessment of Potential for CYP-Inhibition-Based Drug–Drug Interaction Between Vonoprazan and Clopidogrel". . p. 217 - 227. Retrieved 2018/11/10.
• 2、 Shaw, Scott A.,Balasubramanian, Balu,Bonacorsi, Samuel,Cortes, Janet Caceres,Cao, Kevin,Chen, Bang-Chi,Dai, Jun,Decicco, Carl,Goswami, Animesh,Guo, Zhiwei,Hanson, Ronald,Humphreys, W. Griffith,Lam, Patrick Y. S.,Li, Wenying,Mathur, Arvind,Maxwell, Brad D.,Michaudel, Quentin,Peng, Li,Pudzianowski, Andrew,Qiu, Feng,Su, Shun,Sun, Dawn,Tymiak, Adrienne A.,Vokits, Benjamin P.,Wang, Bei,Wexler, Ruth,Wu, Dauh-Rurng,Zhang, Yingru,Zhao, Rulin,Baran, Phil S.. "Synthesis of Biologically Active Piperidine Metabolites of Clopidogrel: Determination of Structure and Analyte Development". . p. 7019 - 7032. Retrieved 2015/07/27.