Regioselective activation of aminothiazole (iminoxyacetic acid) acetic acid: An efficient synthesis of the monobactam aztreonam

…, R Herter, J Wurdinger, P Schierling…

Index: Singh, Janak; Denzel, Theodor W.; Fox, Rita; Kissick, Thomas P.; Herter, Rolf; Wurdinger, Joseph; Schierling, Peter; Papaioannou, Chris G.; Moniot, Jerome L.; Mueller, Richard H.; Cimarusti, Christopher M. Organic Process Research and Development, 2002 , vol. 6, # 6 p. 863 - 868

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Citation Number: 4

Abstract

An efficient synthesis of the monobactam aztreonam [[2 S-[2α, 3β (Z)]]-3 [[(2-amino-4- thiazolyl)[(1-carboxy-1-methylethoxy) imino] acetyl] amino]-2-methyl-4-oxo-1- azetidinesulfonic acid](1) by acylation of α-aminoazetidinone 22 with the regioselectively activated aminothiazoleiminoxyacetic diacid 15 or 18 is described. Reaction of benzhydryl ester 10 with N-hydroxybenzotriazole and dicyclohexylcarbodiimide followed by ester ...