Trifluoroacetic acid → HCID 86604041, compound

Participants

Reaction Conditions

Reaction Steps

2-{(S)-2-[2-tert-Butoxycarbonylamino-2-(3-fluoro-4-methoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester (0.98 g, 2.28 mmol) was taken into dry dichloromethane (20 mL) under argon and cooled in an ice bath. To this was added trifluoroacetic acid (10 mL, 130 mmol) and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was then concentrated to dryness. The oil was dissolved in dichloromethane and precipited with ether and the resulting suspension stirred for 15 minutes. The precipitate was isolated by filtration, washed with ether and dried to give a tan solid. The solid was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic solution was dried over sodium sulfate, filtered, concentrated and dried to give 2-{(S)-2-[2-amino-2-(3-fluoro-4-methoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as a tan foam (0.70 g, 92%).

Provenance & Evidence