Diisopropylethylamine → HCID 67930966, compound

Participants

Reaction Steps

A mixture of 355 mg (0.58 mmol) of (S)-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-1-tritylimidazole-4-propionamide, 95 mg (0.58 mmol) of benzimidazole-2-carboxylic acid [Chem. Ber. 45, 3489 (1912)], 256 mg (0.58 mmol) of BOP and 0.12 ml (0.58 mmol) of Hunig base in 50 ml of acetonitrile is stirred at room temperature for 20 hours. Thereafter, the reaction mixture is evaporated under reduced pressure, the residue is taken up in 60 ml of ethyl acetate and washed twice with 20 ml of saturated potassium hydrogen carbonate solution. After drying the organic phase over sodium sulphate the solvent is evaporated under reduced pressure. For purification, the residue is chromatographed on 30 g of silica gel using a 15:1 mixture of methylene chloride and methanol as the eluent. There are obtained 379 mg of N-[(S)-1-[[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]carbamoyl]-2-(1-tritylimidazol-4-yl)ethyl]-2-benzimidazolecarboxamide as a colourless foam; MS: 751 (M+H)+.

Provenance & Evidence