1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86598954, compound

Participants

Reaction Steps

To a solution of 4′-[3-[(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-phenylethyl]amino]propyl]-3-(cyclohexyloxy)-4-biphenylcarboxylic acid (133 mg) in N,N-dimethylformamide (1.3 ml) was added N,N′-carbonyldiimidazole (41.3 mg) and the mixture was stirred at room temperature for 5 hours. To the mixture were added 1-propanesulfonamide (31.4 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (41.6 μl) and the mixture was stirred at 50° C. for 14 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml×2) and brine (10 ml). The solution was dried over magnesium sulfate then concentrated in vacuo to give a crude solid which was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give tert-butyl [3-[3′-(cyclohexyloxy)-4′-[[(propylsulfonyl)amino]carbonyl]-4-biphenylyl]propyl][(2R)-2-hydroxy-2-phenylethyl]carbamate (63.5 mg) as a white solid.

Provenance & Evidence