Potassium Carbonate → Clopidogrel

HRID 392532Notes

Reaction equation

HRID 392532 reaction equation
Cl.[S:2]1[C:6]2=[CH:7][CH:8]=[CH:9][NH:10][CH:5]2[CH2:4][CH2:3]1.[CH3:11][O:12][C:13](=[O:23])[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:11][O:12][C:13]([C@@H:14]([N:10]1[CH2:9][C:8]2[CH:7]=[CH:6][S:2][C:3]=2[CH2:4][CH2:5]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10730282Methyl alpha-bromo-2-chlorophenylacetateHCID 68420022Tetrahydrothienopyridine hydrochloride

Product 1

HCID 60606Clopidogrel

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Tetrahydrothienopyridine hydrochloride from Example 1 was reacted with α-bromo-2-chlorophenyl acetic acid methyl ester in acetone in the presence of potassium carbonate to give racemic clopidogrel. After inorganic salt filtration, the product was recovered as bisulfate, by addition of sulfuric acid.

Sources & evidence

ORD record
ord-33c9c70198eb41cb9da239572974b3f0
Source dataset
uspto-grants-2004_10
Patent number
US06800759B2

Reaction notes

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