HOAt → (3S)-3-{5-[(Z)-3-(Imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzamido}-5-methylsulfanyl-1-phenyl-2-pentanone

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A solution of pentafluorophenyl 5-[(Z)-3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate (0.25 g, 0.5 mmol), (3S)-5-methylsulfanyl-2-oxo-1-phenylpentan-3amine (0.16 g, 0.6 mmol), 1-hydroxy-7-azabenzotriazole (0.075 g, 0.55 mmol) in DMF (2 ml) was stirred at ambient temperature overnight. After evaporation of the solvent, the residue was taken up in ethyl acetate, washed with 5% sodium hydrogen carbonate and saturated sodium chloride and evaporated to dryness. The residue was then purified by flash chromatography eluting with dichloromethane/ethanol (97/3) to give the title compound which was isolated as the hydrochloride salt by treatment with HCl/ether. Yield: 70%

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