Synthesis of 4-hydroxy-N-[5-(hydroxymethyl)-3-isoxazolyl]-2-methyl-2H-1, 2-benzothiazine-3-carboxamide 1, 1-dioxide and [(5-methyl-3-isoxazolyl) amino] oxoacetic …

…, T Capiris, TP Bobovski, CF Schwender

Index: Sircar, Jagadish C.; Capiris, Thomas; Bobovski, Thomas P.; Schwender, Charles F. Journal of Organic Chemistry, 1985 , vol. 50, # 26 p. 5723 - 5727

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Citation Number: 9

Abstract

In order to confirm the structures of the metabolites, we undertook the synthesis of 2, 3, and 4. Initial attempts to directly brominate the active methine group of isoxicam (1) with bromine in acetic acid gave complex mixtures. Base-catalyzed (n-BuLi) bromination of the isoxicam C3-methine group with NBS in THF followed by treatment with ammonium chloride solution gave 7 as the sole product. Formation of compound 7, which is isomeric to the human ...