Diisopropylethylamine → Clopidogrel

Beteiligte Stoffe

Reaktionsschritte

To a solution of 47.5 g of triphenylphosphine dibromide in 250 ml of acetonitrile, 10 g of 6,7-dihydro-4H-thieno[3,2-c]pyrane was added. The resulting mixture was refluxed for 24 hours, and then added thereto dropwise was a solution obtained by dissolving 14 g of (S)-(+)-2-(2-chlorophenyl)glycine methyl ester hydrochloride and 36 mL of diisopropylethylamine in 100 mL of acetonitrile over 30 minutes while allowing the resulting mixture to reflux. After 8 hours, the reaction product solution was concentrated by evaporation under reduced pressure. To the residue thus obtained, 50 mL of ethyl acetate and 150 mL of n-hexane were added, and the solids thus precipitated were filtered. The filtrate was washed twice with 150 mL portions of water and then with 50 mL of saturated sodium chloride solution. The organic layer was passed through an activated carbon layer and condensed under reduced pressure to obtain 18.6 g (yield of 81%) of the title compound as a yellow oil.

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