Sodium Hydroxide → HCID 69103339, compound

Participants

Reaction Steps

To a solution of methyl 4′-[2-[[tert-butoxycarbonyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]ethyl]-3-isobutyl-4-biphenylcarboxylate (390 mg) in methanol (3.90 ml) and tetrahydrofuran (1.56 ml) was added 1N aqueous sodium hydroxide solution (2.20 ml) and the mixture was stirred at room temperature for 2 days. Methanol and tetrahydrofuran were removed by evaporation under reduced pressure and to the mixture was added ethyl acetate (20 ml). The pH was adjusted to 4.3 with 1N hydrochloric acid and the organic layer was separated, washed with water (20 ml) and brine (20 ml) and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave a crude product which was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/2) to give 4′-[2-[[tert-butoxycarbonyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]amino]-ethyl]-3-isobutyl-4-biphenylcarboxylic acid (291 mg) as a white solid (foam).

Provenance & Evidence