New Procedure for the Preparation of (Z)-2-(5-Amino-1, 2, 4-thiadiazole-3-yl)-2-trityloxyiminoacetic Acid

W Zhong, W Zhang, Y Chen, Y Liu…

Index: Zhong, Weihui; Zhang, Wendong; Chen, Yanhui; Liu, Yanbin; Yao, Yi Organic Process Research and Development, 2011 , vol. 15, # 3 p. 698 - 703

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Citation Number: 3

Abstract

A novel and efficient procedure has been developed for the preparation of the C-7 side chain of ceftobiprole,(Z)-2-(5-amino-1, 2, 4-thiadiazole-3-yl)-2-trityloxyiminoacetic acid (2) from malononitrile (9) in a total yield of 19%. The key intermediate N-(3-(2-acetamido-2- oxoethyl)-1, 2, 4-thiadiazol-5-yl) benzamide (15b) was synthesized for the first time in 76% yield by treatment of N-(3-aminoisoxazol-5-yl) acetamide (13) with benzoyl isothiocyanate. ...