Trifluoroacetic acid → 2-Amino-thiazole-4-carboxylic acid methoxy-methyl-amide

Participants

Reaction Steps

To a solution of [4-(methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester (1.0 g, 3.48 mmol) in dichloromethane (20 mL) was added trifluoroacetic acid (5.0 mL, 64.9 mmol) at 0° C. The reaction was warmed to ambient temperature and stirred for 4 hours. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate and the organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was removed to give 2-amino-thiazole-4-carboxylic acid methoxy-methyl-amide as a foam (585 mg, 90%).

Provenance & Evidence