Sodium → (RS)-Clopidogrel

HRID 434174Notes

Reaction equation

HRID 434174 reaction equation
C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[CH3:16][O:17][C:18](=[O:36])[CH:19]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35])[N:20]1[CH2:25][CH2:24][C:23]2[S:26][CH:27]=[CH:28][C:22]=2[CH2:21]1.[Na]>ClCCl>[CH3:16][O:17][C:18](=[O:36])[CH:19]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35])[N:20]1[CH2:25][CH2:24][C:23]2[S:26][CH:27]=[CH:28][C:22]=2[CH2:21]1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 156143992-chlorophenyl(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester (-)-camphorsulfonic acid salt

Product 1

HCID 2806(RS)-Clopidogrel

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the suspension made of 200 g of (+)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester (−)-camphorsulfonic acid salt and 800 ml of dichloromethane is added 800 ml of sodium hydrogene carbonate solution. After stirring the organic phase is separated by decantation. The (+)-(2-chlorophenyl)(6,7-dihydro-4H-thieno[3,2-c]pyridin-5-yl)acetic acid methyl ester is obtained as a solution in 800 ml of dichloromethane. The solution is dried over sodium sulfate and the solvent is removed in vacuo.

Workup

  1. customis separated by decantation

Sources & evidence

ORD record
ord-cf8105d8b93e486fbcba025e00c2acdf
Source dataset
uspto-grants-2003_12
Patent number
US06670486B1

Reaction notes

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