A Convenient Synthesis of Carbapenem Antibiotic Ertapenem Sodium

摘要

A convenient synthesis of ertapenem sodium is described. The starting material, trans-hydroxyproline, was converted to N-diisopropoxyphosphoryl hydroxyproline (5), mesylation of the hydroxyl group and activation of the carboxyl group in 5 by using methanesulfonyl chloride afforded intermediate 6, aminolysis of the mixed anhydride 6 with allyl 3-aminobenzoate gave compound 8, treatment of the methanesulfonate (8) with potassium thioacetate gave key intermediate compound 4. The compound 4 was deacetylated and then coupled with enol phosphate 2, followed by cleavage of protecting groups affording ertapenem in an overall yield of 39.2 %.