Hydrochloric Acid → HCID 86598958, compound

Participants

Reaction Steps

To a solution of 4′-[2-[[tert-butoxycarbonyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-isobutoxy-4-biphenylcarboxylic acid (170 mg) in N,N-dimethylformamide (1.70 ml) was added 1,1′-carbonylbis(1H-imidazole) (61.7 mg) and the mixture was stirred at room temperature for 1 hour under nitrogen atmosphere. To the reaction mixture were added methanesulfonamide (36.3 mg) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (0.057 ml) and the mixture was stirred at 120° C. for 12 hours. After cooling to room temperature, to the reaction mixture was added water (10 ml) and the pH was adjusted to 5.98 with 0.1N hydrochloric acid. The mixture was extracted with ethyl acetate (twice), washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude produce which was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1.5) and further purification by column chromatography on silica gel (eluent: chloroform/methanol=100/0 to 99/1) gave tert-butyl [(2R)-2-hydroxy-2-(3-pyridyl)ethyl][2-[3′-isobutoxy-4′-[[(methylsulfonyl)amino]carbonyl]-4-biphenylyl]ethyl]carbamate (63 mg) as a white foam.

Provenance & Evidence