Acetaldehyde → HCID 70049907, compound

Participants

Reaction Steps

Sodium cyanoborohydride (45 mg) was added in one portion to a stirred, ice cold solution of N-{1-[2-(S)-t-butyloxycarbonyl-3(N6 -t-butyloxycarbonyl-(S)-lysylamino)propyl]-1-cyclopentanecarbonyl}O-t-butyl-(S)-tyrosine-t-butyl ester (507 mg) and acetaldehyde (31 mg) in aqueous ethanol (80%, 10 ml) and the pH adjusted to 5 with 1N hydrochloric acid. The resulting solution was allowed to warm to room temperature and stirred for 1.5 hours. The reaction mixture was evaporated to dryness and the residue partitioned between water and ethyl acetate. The phases were separated and the organic phase washed with a little aqueous sodium bicarbonate, dried (MgSO4), filtered and evaporated. The residue was chromatographed over silica gel, eluting with mixtures of hexane and ethyl acetate containing 1% diethylamine to yield the title compound as an oil (370 mg, 64%) Rf 0.55 (silica; CH2Cl2, CH3OH, NH4OH; 90:10:1).

Provenance & Evidence