HCID 178418546, compound → HCID 178455620, compound

Participants

Reaction Steps

A solution of 335 mg (0.44 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R, 3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-5-iodoimidazole-4-propionamide and 79 mg (0.88 mmol) of copper-(I) cyanide in 25 ml of dimethylformamide is stirred at 120° overnight under argon. Subsequently, the reaction mixture is evaporated under reduced pressure, the residue is suspended in 30 ml of a 95:5 mixture of methylene chloride and methanol and filtered over Dicalite. The filtrate is evaporated and, for purification, the residue is chromatographed on 50 g of silica gel using a 160:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. After precipitation from a methylene chloride-ether mixture there are obtained 40 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-5-cyanoimidazole-4-propionamide as a colourless powder; MS: 656 (M+H)+.

Provenance & Evidence