139714-26-4Relevant articles and documents
Regioselective activation of aminothiazole(iminoxyacetic acid)acetic acid: An efficient synthesis of the monobactam aztreonam
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.
, p. 863 - 868 (2002)
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-hydroxy-benzotriazole 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.