Methanol → 3-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-phenylquinoline-6-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-phenylquinoline-6-carboxylate (0.58 g, 1.3 mmol) in tetrahydrofuran (6 ml)-methanol (6 ml) was added 1N aqueous sodium hydroxide solution (3 ml), and the mixture was stirred at 50° C. for 2 hrs. The reaction mixture was partitioned between tetrahydrofuran (50 ml)-ethyl acetate (50 ml) and 0.1N hydrochloric acid (100 ml) and the aqueous layer was extracted twice with tetrahydrofuran (25 ml)-ethyl acetate (25 ml). The organic layers were combined, washed with saturated brine (50 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from diisopropyl ether-ethyl acetate to give 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-phenylquinoline-6-carboxylic acid (0.56 g, 99%) as colorless crystals.

Provenance & Evidence