Benzoyl chloride → HCID 70080082, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [[(R,S)-methoxy-[N-(N-(benzyloxycarbonyl)-L-prolyl)aminobutyl]phosphinyl]methyl]-4-phenylbutanoyl-L-leucine N-phenylamide (169 mg, 0.226 mmol) in methanol (2 mL) was stirred for 6 hours under an atmosphere of hydrogen in the presence of 20% palladium hydroxide-on-carbon (34 mg). The catalyst was removed by filtration through Celite, the filter washed with methanol, and the combined filtrate and washings evaporated. The resulting amine was dried under high vacuum, then dissolved in methylene chloride (2 mL), cooled to 0° C. and treated with benzoyl chloride (29 ml, 0.25 mmol) and N-methylmorpholine (27 μl, 0.25 mmol) at 0° C. for 90 min. The reaction mixture was diluted with ethyl acetate (25 mL), washed with 2N hydrochloric acid, saturated brine solution, dried (magnesium sulfate), and evaporated. Purification was achieved by flash chromatography on silica gel using initially 2% methanol in methylene chloride and subsequently 3% methanol in methylene chloride; yield 101 mg (62%); FAB MS: m/z 716 (M+1).

Provenance & Evidence