Citric Acid → HCID 66907788, compound

Participants

Reaction Conditions

Reaction Steps

To a mixed solution of ethyl 2-[4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]cyclopropanecarboxylate (0.451 g, 0.892 mmol) in ethanol (2 mL) and tetrahydrofuran (4 mL) was added 2 M aqueous sodium hydroxide solution (1 mL), and the mixture was stirred at 50° C. for 7 hr. Water was added to the reaction mixture, and the mixture was mildly-acidified with 10% aqueous citric acid solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-100:0) to give a yellow oil. To a solution of the obtained oil in ethyl acetate (3.2 mL) was added 4 M hydrogen chloride/ethyl acetate solution (0.8 mL) and the mixture was concentrated under reduced pressure. The residue was crystallized from diethyl ether-ethyl acetate to give the title compound (0.349 g, yield 73%) as colorless crystals.

Provenance & Evidence