Potassium Carbonate → Clopidogrel

HRID 854612Notes

Reaction equation

HRID 854612 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-bfb6021ed1ef404e8940be3679ac995a
Source dataset
uspto-grants-2007_08
Patent number
US07259261B2

Reaction notes

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