Practical Preparation of (Z)-2-(5-Amino-1, 2, 4-thiadiazol-3-yl)-2-methoxyiminoacetic Acid: A Side-Chain of the Fourth Generation of Cephem Antibiotics.

…, T Tamai, R Yoshida, T Inagaki, Y Kurita

Index: Tatsuta; Miura; Gunji; Tamai; Yoshida; Inagaki; Kurita Bulletin of the Chemical Society of Japan, 1994 , vol. 67, # 6 p. 1701 - 1707

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Citation Number: 16

Abstract

A Z-isomer (4) of 2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2-(methoxyimino) acetic acid, which is the common acyl moiety of clinically useful cephem antibiotics, has been prepared from the aminoisoxazoles through the skeletal rearrangement in several routes. Reaction of 3-amino- 5-methoxyisoxazole (7) with alkoxycarbonyl isothiocyanates gave methyl 2-(5- alkoxycarbonylamino-1, 2, 4-thiadiazol-3-yl) acetates (8), which were converted into the ...