Potassium Hydroxide → 3-[2,6-Difluoro-4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]propanoic acid

Participants

Reaction Steps

That is, ethyl 3-[2,6-difluoro-4-[[4-[[(2-phenylethyl)(4-phenyl-1,3-thiazol-2-yl)amino]methyl]benzyl]oxy]phenyl]-propanoate (300 mg, 0.49 mmol) was dissolved in a mixed solvent of tetrahydrofuran (8 mL) and ethanol (8 mL). Thereto was added an aqueous solution (5 mL) of 85% potassium hydroxide (100 mg, 1.51 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and crystallized from diethyl ether-hexane to give the title compound (271 mg, yield 94%) as colorless prism crystals.

Provenance & Evidence