Acetic Acid → 3,5-Dioxohexanoic acid

Participants

Reaction Steps

The resulting fully protected dipeptide ester is treated with 1/1 trifiuoroacetic acid/dichloromethane at room temperature, neutralized with saturated aqueous sodium bicarbonate solution, and extracted into ethyl acetate. Evaporation gives the partially deblocked dipeptide, which is redissolved in dry THF and added to a stirring solution of benzyloxycarbonylglycine, N-methylmorpholine, and isobutyl chloroformate in dry THF at -15° C. The formed, fully protected tripepride ester is totally deblocked by treatment with hydrogen gas in glacial acetic acid at room temperature in the presence of Pd-C catalyst. Filtration, evaporation and purification on a microcrystalline cellulose column followed by lyophilization give the desired tripepride ester as its triacetate salt.

Provenance & Evidence