1,2-Dichloroethane → N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester

Participants

Reaction Steps

To a solution of 2-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid (220 mg, 0.533 mmol) and the amine hydrochloride salt from step C (212 mg, 0.533 mmol), HOBT (72 mg, 0.533 mmol), and N-methylmorpholine (117 μl, 1.11 mmol) in DMF (2 ml) was added EDC (764 mg, 3.99 mmol). The reaction was stirred at room temperature for 72 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine, dried (Na2SO4). and evaporated in vacuo. The residue was chromatographed (SiO2, 3-4% MeOH in CH2Cl2, gradient elution) to afford the title compound as a white solid.

Provenance & Evidence