Sodium Bicarbonate → (RS)-Clopidogrel

HRID 1384484Notes

Reaction equation

HRID 1384484 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.C(=O)([O-])O.[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 516892Sodium BicarbonateHCID 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 hydrogen carbonate solution. After stirring the organic phase is separated by decantation, dried on sodium sulfate and the solvent is removed in vacuo. 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. After stirring, the organic phase is separated by decantation, dried over sodium sulfate and the solvent is removed in vacuo.

Workup

  1. customis separated by decantation
  2. customdried on sodium sulfate
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-d4d1f8c5c6a04ba8bbc1e5b18bd2c1d1
Source dataset
uspto-grants-2001_07
Patent number
US06258961B1

Reaction notes

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