Potassium Carbonate → HCID 86751644, compound

Participants

Reaction Steps

A suspension of 250 mg (0.4 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]imidazole-4-propionamide, 60 mg of 18-crown-6, 250 mg of potassium carbonate and 2 ml of chloromethyl pivalate is stirred at room temperature overnight. Thereafter, the reaction mixture is taken up in ethyl acetate and the ethyl acetate solution is washed with saturated ammonium chloride solution. After drying over sodium sulphate the solution is evaporated under reduced pressure and subsequently, for purification, the crude product obtained (1.3 g) is chromatographed on 120 g of silica gel using a 200:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. There are obtained 145 mg of [4-[(S)-2-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-2-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]ethyl]imidazol-1-yl]methyl pivalate as a colourless solid; MS: 745 (M+H)+.

Provenance & Evidence