Triethylamine → tert-Butyl (4-(methoxy(methyl)carbamoyl)thiazol-2-yl)carbamate

Participants

Reaction Steps

2-tert-Butoxycarbonylamino-thiazole-4-carboxylic acid (10.44 g, 42.74 mmol), N,O-dimethylhydroxylamine hydrochloride (5.0 g, 51.26 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (9.83 g, 51.28 mmol), 1-hydroxybenzotriazole hydrate (6.93 g, 51.28 mmol), triethylamine (7.15 ml, 51.28 mmol) and 4-(dimethylamino)pyridine (1.04 g, 8.52 mmol) were combined in dichloromethane (200 mL) and stirred overnight at room temperature. The resulting solution was poured into ethyl acetate and washed with 0.2 M aqueous hydrochloric acid, water, brine and dried over magnesium sulfate. Solvent was removed and the crude was by purified over silica gel eluted with 80% v/v ethyl acetate in hexane to give [4-(methoxy-methyl-carbamoyl)-thiazol-2-yl]-carbamic acid tert-butyl ester as a foam (17.0 g, 95%).

Provenance & Evidence