Ethyl Acetate → Clopidogrel Impurity 7

HRID 988852Notes

Reaction equation

HRID 988852 reaction equation
[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C@H:23]([N:27]1[CH2:32][CH2:31][C:30]2[S:33][CH:34]=[CH:35][C:29]=2[CH2:28]1)[C:24]([NH2:26])=[O:25].C(OCC)(=O)C>O.C(=O)(O)[O-].[Na+]>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C@H:23]([N:27]1[CH2:32][CH2:31][C:30]2[S:33][CH:34]=[CH:35][C:29]=2[CH2:28]1)[C:24]([NH2:26])=[O:25]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 131724105HCID 131724105, compound

Product 1

HCID 9944392Clopidogrel Impurity 7

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To the suspension of 1.8 g of (S)-(+)-(2-chloro-phenyl)-(6,7-dihydro-4H-thieno[3,2-c]pyrid-5-yl) acetamide (1S)-(+)-camphor-10-sulfonic acid salt in 100 mL water, 50 mL of sodium bicarbonate solution in water was added. After stirring the mixture, 150 mL ethyl acetate was added. The combined organic layers are distilled off to get title product. The amount of product obtained was 1 g (56%).

Workup

  1. additionwas added
  2. additionwas added
  3. distillationThe combined organic layers are distilled off

Sources & evidence

ORD record
ord-5e254684b9db49e4b0086f49e8a8f3fa
Source dataset
uspto-grants-2003_10
Patent number
US06635763B2

Reaction notes

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