Acetic Anhydride → HCID 67684739, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-t-butoxycarbonyl-S-trityl-L-Cysteinyl4-benzyl-4-piperidinol (100 mg, 0.16 mmol) in dry pyridine (2 ml), was added 4-dimethylaminopyridine (25 mg, 0.20 mmol) and acetic anhydride (0.030 ml, 0.32 mmol). The solution was heated to 50° C. (oil bath temp.) for 2 days and then allowed to cool to room temp. The reaction mixture was concentrated in vacuo and the residue partitioned between EtOAc and brine. The EtOAc layer was dried (MgSO4) and concentrated in vacuo to a brown oil. This material was purified by column chromatography on silica with 18-20% EtOAc/hexane as eluent. The appropriate fractions were combined and concentrated in vacuo to afford the product as a glassy solid.

Provenance & Evidence