2-bromo-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-Thiazolecarboxylic acid synthesis

Yield:1312697-86-1 70%

Reaction Conditions:

with N-Bromosuccinimide in dichloromethane at 20; for 1 h;

Steps:

To a solution of 5-(tert-butoxycarbonylamino)thiazole-4-carboxylic acid (1.72 g, 10 mmol) in DCM (50 mL) was added in three portions NBS (1.95 g, 11 mmol); the reaction mixture was stirred at ambient temperature for 1 h. Reaction was concentrated in vacuo; resulted residue was purified by silica gel column chromatography (6:1 Pet-ether-EtOAc) to afford 2-bromo-5-(tert-butoxycarbonylamino)thiazole-4-carboxylic acid (1.75 g, 70%) as white solid: ¹H-NMR (CDCl₃, 500 MHz) δ (ppm): 13.65 (s, 1H), 10.03 (s, 1H), 1.49 (s, 9H). MS (ESI) m/z: 324 [M+H⁺]

References:

Wang, Xiaojing;Ebens, JR., Allen J. US2011/59961, 2011, A1 Location in patent:Page/Page column 44

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