Hexane → Clopidogrel

Participants

Reaction Steps

5.0 g of 2-(2-bromoethyl)-3-bromomethylthiophene obtained in Example 7 was dissolved in 50 mL of acetonitrile, and added thereto was a solution obtained by dissolving 4.6 g of (S)-(+)-2-(2-chlorophenyl)glycine methyl ester hydrochloride and 6.8 g of diisopropylethylamine in 20 mL of acetonitrile over 30 minutes. The resulting mixture was refluxed for 8 hours, and concentrated by evaporation under reduced pressure. The residue was dissolved in 100 mL of ethyl acetate, and washed twice with 70 mL portions of water. The organic layer was washed with 50 mL of saturated sodium chloride aqueous solution and condensed under reduced pressure. The dark yellow colored oily residue thus obtained was subjected to a silica gel column chromatography (eluent, n-hexane:ethyl acetate=5:1) to obtain 5.0 g (yield of 88%) of the title compound as a yellowish oil.

Provenance & Evidence