Regioselective Activation of Aminothiazole(iminoxyacetic acid)acetic Acid: An Efficient Synthesis of the Monobactam Aztreonam
Organic Process Research & Development2002Vol. 6(6), pp. 863–868
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Janak Singh, Theodor Denzel, Rita Fox, Thomas P. Kissick, Rolf Herter, Joseph Wurdinger, Peter Schierling, Chris G. Papaioannou, Jerome L. Moniot, Richard H. Mueller, C. M. CIMARUSTI
Abstract
An efficient synthesis of the monobactam aztreonam [[2S-[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 deprotection formed the monoacid amide 15. Alternatively, chemoselective transient silylation of the diacid 9 followed by activation with N-hydroxysuccinimide formed active ester 18. Acylation of α-aminoazetidinone 22 with amide 15 or ester 18 produced aztreonam (1) in 75−85% yield.
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