反应详情

To a solution of ethyl(+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoate (95 mg, 0.24 mmol) in methanol (1.2 mL) and tetrahydrofuran (1.2 mL) was added 1 N aq sodium hydroxide (1.2 mL, 1.2 mmol). After 17 hours, the solution was concentrated under reduced pressure to remove methanol and tetrahydrofuran. The mixture was then acidified to pH 5 with 1 N aq hydrochloric acid and diluted with sat. aq sodium chloride (20 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give (+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid. 1HNMR (400 MHz, CD3OD) δ 8.50 (br. s, 1H), 8.02 (d, J=8.2 Hz, 2H), 7.80-7.73 (m, 1H), 7.57 (d, J=8.2 Hz, 2H), 7.53-7.47 (m, 1H), 7.40-7.32 (m, 2H), 6.95 (d, J=2.5 Hz, 1H), 4.73-4.64 (m, 1H), 2.55-2.39 (m, 1H), 2.39-2.22 (m, 1H), 2.22-2.04 (m, 2H).

1. concentrationthe solution was concentrated under reduced pressure
2. customto remove methanol and tetrahydrofuran
3. additiondiluted with sat. aq sodium chloride (20 mL)
4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure