Sodium Hydroxide → HCID 178468418, compound

Participants

Reaction Steps

66 mg (0.19 mmol) of ethyl 4-cyclohexylpiperidine-4-carboxylate trifluoroacetate are diluted in 3 mL of dichloromethane and 3 mL of dimethylformamide, and 67 mg (0.21 mmol) of TBTU and 75 mg (0.21 mmol) of 2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionic acid and 0.06 mL (0.38 mmol) of diisopropylethylamine are added. After 2 hours of stirring at room temperature, aqueous 1N NaOH solution is added and the organic products are extracted with dichloromethane. The organic phase is dried and then evaporated. The crude product obtained is chromatographed on silica gel (eluent: 95/5 dichloromethane/methanol). 34 mg of ethyl 4-cyclohexyl-1-[2-{3-ethyl-3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylate in the form of a yellow oil are obtained in a yield of 30%.

Provenance & Evidence