N,N-Dimethylaniline → HCID 11251187, compound

Participants

Reaction Steps

To a solution of diethyl 2-hydroxymethyl-2-phenylmalonate (179 mg) and N,N-dimethylaniline (122 mg) in chloroform was added triphosgene (80 mg) under ice-cooling, and the mixture was stirred at room temperature, and after 3 hours, added dropwise to a solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-5-fluoro-4-hydroxyphenyl)amide (200 mg) and triethylamine (68 mg) in THF under ice-cooling. The mixture was stirred at room temperature for 2 hours, and then diluted with ethyl acetate. The extract was washed successively with saturated aqueous sodium bicarbonate and saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 2-{5-dimethylcarbamoyl-2-fluoro-4-[(4′-trifluoromethylbiphenyl-2-carbonyl)amino]phenoxycarbonyloxymethyl}-2-phenylmalonic acid diethyl ester (88 mg).

Provenance & Evidence