Trifluoroacetic acid → HDTrp-MeLeu-MetNH2

Participants

Reaction Steps

Condensation of BocMeLeuOH (5.0 g.) and HMetNH2 (3.7 g.) by the mixed anhydride method using diphenylphosphinyl chloride gave BocMeLeu-MetNH2 in 67% yield. De-t-butoxycarbonylation of BocMeLeu-MetNH2 (5.2 g.) using hydrogen chloride in ethyl acetate gave HMeLeu-MetNH2 in 90% yield. Condensation of BocDTrpOPFP (5.60 g.) and HMeLeu-MetHN2 (3.70 g.) by the activated ester method gave BocDTrp-MeLeu-MetNH2 in 55% yield. De-t-butoxycarbonylation of BocDTrp-MeLeu-MetNH2 (3.38 g.) using trifluoroacetic acid in dimethyl sulfide and ethanedithiol gave HDTrp-MeLeu-MetNH2 in 74% yield.

Provenance & Evidence