Journal of Organic Chemistry p. 5723 - 5727 (1985)
Update date:2022-08-05
Topics:
Sircar, Jagadish C.
Capiris, Thomas
Bobovski, Thomas P.
Schwender, Charles F.
4-Hydroxy-N-<5-(hydroxymethyl)-3-isoxazolyl>-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (2), the major oxidative human metabolite of isoxicam (1), and <(5-methyl-3-isoxazolyl)amino>oxoacetic acid (3), the major rat metabolite of isoxicam (1), were synthesized. 2 was synthesized by condensation of the known benzothiazine ester 8 with the isoxazolamine 9b. 9b was synthesized via a nine-step sequence starting with 5-methyl-3-isoxazolecarboxylic acid (14).NBS bromination of 14 gave 5-(bromomethyl)-3-isoxazolecarboxylic acid, which was coverted to the carbamate ester via a Curtius rearrangement of the acid azide.Displacement of bromine with silver acetate gave the acetoxy compound 21.Hydrolysis of 21 gave the unstable 3-isoxazolamine derivative 9a, which was converted to the OSiMe3 derivative 9b.The compound 3 was synthesized by reaction of ethyl oxalyl chloride with 5-methyl-3-isoxazolamine followed by base hydrolysis.
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