Pyridinium hydrochloride → HCID 178523870, compound

Participants

Reaction Steps

A mixture of 375 mg (0.39 mmol) of (S)-α-2-benzimidazolecarboxamido-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-tritylimidazole-4-propionamide and 1.8 g (15.6 mmol) of pyridinium hydrochloride in 40 ml of methanol is heated to reflux for 3.5 hours. Thereafter, the reaction mixture is evaporated and the residue is partitioned between 100 ml of ethyl acetate and 50 ml of water. The organic phase is washed with 100 ml of semi-saturated ammonium chloride solution and 100 ml of 2N potassium bicarbonate solution, thereafter dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue is chromatographed on 40 g of silica gel using a 6:1 mixture of methylene chloride and methanol as the eluent. There are obtained 110 mg of N-[(S)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-imidazol-4-ylethyl]-2-benzimidazolecarboxamide as an amorphous solid; MS: 509 (M+H)+.

Provenance & Evidence