Potassium Carbonate → Clopidogrel

HRID 1582570Notes

Reaction equation

HRID 1582570 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-3bcbba1a7c0e4063bb43d4bfa6494274
Source dataset
uspto-grants-2004_05
Patent number
US06737411B2

Reaction notes

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