Trifluoroacetic acid → HCID 66679712, compound

Participants

Reaction Steps

4 mL of TFA was added at room temperature to 350 mg (0.77 mmol) of methyl 2-({[4-(adamantan-1-ylcarbonyl)phenyl]carbonyl}amino)-5-chlorobenzoate obtained in Example 56-(ii). 360 mg (3.1 mmol) of triethyl silane was added thereto, and the mixture was stirred for 17 hours. The reaction mixture was diluted with ethyl acetate, and washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel chromatography, thereby giving 70 mg of methyl 2-({[4-(adamantan-1-ylmethyl)phenyl]carbonyl}amino)-5-chlorobenzoate (yield: 21%) and 262 mg of methyl 2-{[(4-{adamantan-1-yl[(trifluoro-acetyl)oxy]methyl]phenyl)carbonyl}amino}-5-chlorobenzoate (yield: 62%).

Provenance & Evidence