Dimethyl Sulfide → HDTrp-Leu-MetNH2 acetate

Participants

Reaction Conditions

Reaction Steps

BocDTrp-Leu-MetNH2 (47.5 mmole) was added to a solution of trifluoroacetic acid (230 ml.), dimethylsulfide (260 ml.) and ethanedithiol (20 ml.) with cooling to 0° C. The mixture was allowed to warm to room temperature during one and one half hours, then stripped of volatiles. Attempted crystallization of the residue from ethyl acetate-hexane was unsuccessful, and the mixture was stripped again. The residue was dissolved in methanol-ether. Removal of a small amount (about 300 mg.) of solid and addition of acetic acid to the filtrate afforded HDTrp-Leu-MetNH2 acetate salt in 60% yield (12.6 g., m.r. 154°-160° C.).

Provenance & Evidence