Methanol → (S)-N-Benzyl-N-methyl-2-[[(S)-2-[(1H-indol-3-yl)-1-carboxymethyl]-ethylamino]-N'-(t-butoxycarbonyl)-ethylamino]-3-phenyl-propionamide

Participants

Reaction Steps

Combine (S)-N-benzyl-N-methyl-2-[N'-(t-butoxycarbonyl)-2-oxo-ethylamino]-3-phenyl-propionamide (4.87 g, 11.87 mmol) and (S)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamine hydrochloride salt ((S)-tryptophan methyl ester hydrochloride salt) (3.02 g, 11.86 mmol) in methanol (120 mL). Add dropwise, a solution of sodium cyanoborohydride (9.5 mL, 1M in THF, 9.5 mmol) and stir under an inert atmosphere for 48 hours. Concentrate in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 3% methanol/dichloromethane to give the title compound: TLC Rf =0.57 (silica gel, 10% methanol/dichloromethane).

Provenance & Evidence