Citric Acid → 2-[2-(3,5-Bis-trifluoromethyl-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid

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Reaction Steps

A solution of 2-[2-(3,5-bis-trifluoromethyl-phenyl)-6-(4-trifluoromethyl-phenyl)-pyridin-4-yl]-4-methyl-pentanoic acid methyl ester (80 mg, 0.14 mmol) in NaOH (1N, 1 mL) and THF (4 mL) was stirred at 40° C. overnight. The mixture was cooled to room temperature, acidified with 10% citric acid, extracted with CH2Cl2 (3×). The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (5-30% ethyl acetate in CH2Cl2) to give the product as a white solid (60 mg, 78%). 1H NMR (300 MHz, CDCl3) δ 8.55 (s, 2H), 8.23 (d, J=7.91 Hz, 2H), 7.96 (s, 1H), 7.72-7.85 (m, 4H), 3.89 (t, J=7.91 Hz, 1H), 2.08-2.22 (m, 1H), 1.75-1.85 (m, 1H), 1.55-1.68 (m, 1H), 0.99 (d, J=6.40 Hz, 6H). MS m/e 550.2 (M+H).

Provenance & Evidence