Hydrochloric Acid → HCID 57213565, compound

Participants

Reaction Steps

To a solution of (3S)-3-[(2S)-5-benzyloxycarbonyl-2-aminopentanoyl]oxyhexadecanamide hydrochloride (2.17 g) in dichloromethane (8 ml) were added phenyl chlorocarbonate (0.65 ml) and triethylamine (1.68 ml). This mixture was stirred at room temperature overnight, and then poured into a mixture of ethyl acetate (80 ml) and 1N hydrochloric acid (80 ml). The organic layer was washed with water, saturated aqueous sodium bicarbonate, and brine successively. This solution was dried and evaporated to dryness. The residue was chromatographed on silica gel (200 cc) eluting with a mixture of dichloromethane and methanol (20:1) to give (3S)-3-[(2S)-5-benzyloxycarbonyl-2-(phenoxycarbonylamino)-pentanoyl]oxyhexadecanamide (1.73 g).

Provenance & Evidence