Methanol → 3-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Participants

Reaction Steps

To a solution of ethyl 3-(6-amino-1H-benzimidazol-1-yl)-3-phenylpropanoate (150 mg, 485 μmol) in methanol (6 mL) was added phenyl isocyanate (50 μL, 460 μmol) and N,N-diisopropylethylamine (80 μL, 459 μmol). The solution was stirred at room temperature for 48 hours, and additional aliquots of phenyl isocyanate (10 μL, 92 μmol) and N,N-diisopropylethylamine (16 μL, 92 μmol) were added. The solution was stirred at room temperature for an additional 24 hours, and was then evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5) to afford the title compound, [LCMS (Method A, Mobile Phase II) RT 5.13 min, MH+ 415].

Provenance & Evidence