Trifluoroacetic acid → (3R)-3-({[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoic acid

Participants

Reaction Steps

Trifluoroacetic acid (2.5 mL) was added dropwise over 5 min to a stirred solution of tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate (550 mg, 0.9 mmol) in anhydrous dichloromethane (5 mL) under nitrogen at 20° C. The solution was stirred for 1 h and concentrated under reduced pressure. The residue was diluted with hydrochloric acid (2M) and extracted with three portions of ethyl acetate. The combined organic solutions were washed with saturated aqueous sodium chloride, dried (MgSO4) and concentrated under reduced pressure. Two portions of toluene were added and evaporated to give the title compound as a yellow gum (640 mg), contaminated with toluene and trifluoroacetic acid.

Provenance & Evidence