Citric Acid → HCID 178468425, compound

Participants

Reaction Steps

To 65 mg (0.141 mmol) of ethyl 4-cyclohexyl-1-[(R)-2-isothiocyanato-3-(4-methoxy-phenyl)propionyl]piperidine-4-carboxylate in 5 ml of DMF are added 50 mg (0.141 mmol) of 3-(1H-imidazol-4-yl)propylamine bis(trifluoroacetate) (cf. preparation 4-2) and then 0.063 ml (0.425 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction medium is stirred for 2 hours and then hydrolysed by adding aqueous 5% citric acid solution. The organic compounds are extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and concentrated. The crude product obtained is chromatographed on silica gel (eluent: 80/20 CH2Cl2/MeOH). 22 mg of ethyl 4-cyclohexyl-1-[(R)-2-{3-[2-(1H-imidazol-4-yl)propyl]thioureido}-3-(4-methoxy-phenyl)propionyl]piperidine-4-carboxylate in the form of a pale yellow powder are obtained in a yield of 26%.

Provenance & Evidence