Z. Ai
2006
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Journal
Chinese Journal of Pharmaceuticals
Abstract
Doripenem was synthesized by the condensation of (2S,4S) -1-t-butoxycarbonyl-2- (N-t-butoxycarbonyl-sulfamoylamido) methyl-4-mercaptopyrrolidine (7) and (1R,5S,6S) -6- [(1R) -1-hydroxyethyl] -2-diphenoxyphosphonyloxy-l-methyl-l-carba-2-penem-3-carboxylic acid p-nitrobenzylester (8) , followed by deprotection with a yield of 50.5 %. Compound 7 was obtained from trans-4-hydroxy-L-proline by esterificatiom, protection, reduction, SN2 substitution, Mitsunobu reaction and alcoholysis with a yield of 50.8 %. The overall yield was about 26 % (based on trans-4-hydroxy-L-prorine).