2-Oxo Clopidogrel Hydrochloride(Mixture of diastereomers)

Base Information

• Chemical Name: 2-Oxo Clopidogrel Hydrochloride (Mixture of diastereomers)
• CAS No.: 109904-27-0
• Molecular Formula: C₁₆H₁₆ClNO₃S
• Molecular Weight: 337.827
• Mol file: 109904-27-0.mol

Synonyms:2-Oxo Clopidogrel Hydrochloride(Mixture of diastereomers);a-(2-Chlorophenyl)-2,6,7,7a-tetrahydro-2-oxo-thieno[3,2-c]pyridine-5(4H)-acetic Acid Methyl Ester Hydrochlorid;α-(2-Chlorophenyl)-2,6,7,7a-tetrahydro-2-oxo-thieno[3,2-c]pyridine-5(4H)-acetic Acid Methyl Ester Hydrochloride;a-(2-Chlorophenyl)-2,6,7,7a-tetrahydro-2-oxo-thieno[3,2-c]pyridine-5(4H)-acetic Acid Methyl Ester Hydrochloride

Chemical Property of 2-Oxo Clopidogrel Hydrochloride(Mixture of diastereomers)

Chemical Property:

• Melting Point: 133-1350C
• 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: 3.56810
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%min ^*data from raw suppliers

2-Oxo Clopidogrel Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The essential intermediate metabolite from which the active metabolite of Clopidogel is formed 2-Oxo Clopidogrel is the essential intermediate metabolite from which the active metabolite of Clopidogel is formed.

Technology Process of 2-Oxo Clopidogrel Hydrochloride(Mixture of diastereomers)

There total 32 articles about 2-Oxo Clopidogrel Hydrochloride(Mixture of diastereomers) 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: 62.0%

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) + methyl 2-bromo-2-(2-chlorophenyl)acetate (85259-19-4,622835-93-2,66504-71-0) → (SR)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate (109904-27-0)

Guidance literature:

With potassium hydrogencarbonate; In acetonitrile; at 20 ℃;

DOI:10.3390/molecules23051041

Reference yield: 44.0%

methyl 2-chloro-2-(2-chlorophenyl)acetate (90055-47-3) + 5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride (115473-15-9) → (SR)-methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno-[3,2-c]pyridin-5(2H,4H,6H)-yl)acetate (109904-27-0)

Guidance literature:

5,6,7,7a-tetrahydro-thieno[3,2-c]pyridin-2(4H)-one hydrochloride; With potassium hydrogencarbonate; sodium iodide; In N,N-dimethyl-formamide; at 55 ℃; for 0.05h; Inert atmosphere;

methyl 2-chloro-2-(2-chlorophenyl)acetate; In N,N-dimethyl-formamide; at 55 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1021/acs.joc.5b00632

upstream raw materials:

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

methyl 2-bromo-2-(2-chlorophenyl)acetate

rac-methyl 2-chloromandelate

methyl 2-chloro-2-(2-chlorophenyl)acetate

Downstream raw materials:

cis-5-thiol metabolite

methyl (7aR,2'S)-2-(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydrothieno[3,2-c]-5-pyridin-2-one)acetate

methyl (7aS,2'S)-2-(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydrothieno[3,2-c]-5-pyridin-2-one)acetate

methyl (7aS,2'S)-2-(2-chlorophenyl)-2-(2,4,5,6,7,7a-hexahydrothieno[3,2-c]-5-pyridin-2-one)acetate hydrogen sulfate

Refernces

• 1、 Lu, Nan,Li, Lingjun,Zheng, Xuemin,Zhang, Shijun,Li, Yuquan,Yuan, Jing,Wei, Qunchao,Xu, Youjun,Meng, Fancui. "Synthesis of a novel series of amino acid prodrugs based on thienopyridine scaffolds and evaluation of their antiplatelet activity". . . Retrieved 2018.
• 2、 -. "STABLE COMPOSITIONS OF (7AS,2'S)-2-OXOCLOPIDOGREL AND ITS PHARMACEUTICAL SALTS". Page/Page column 30; 31. . Retrieved 2021/04/17.