Sodium Hydroxide → HCID 71239373, compound

Participants

Reaction Steps

To a solution of ethyl(+/−)-3-(4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzamido)propanoate (74 mg, 0.16 mmol) in methanol (0.78 mL) and tetrahydrofuran (0.78 mL) was added 1 N aq sodium hydroxide (0.78 mL, 0.78 mmol). After 10 minutes, the solution was concentrated under reduced pressure to remove methanol and tetrahydrofuran. The mixture was then acidified to pH 4 with 1 N aq hydrochloric acid and diluted with sat. aq sodium chloride (10 mL). The aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give (+/−)-3-(4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzamido)propanoic acid. 1HNMR (400 MHz, DMSO-d6) δ 12.18 (br. s., 1H), 8.56 (d, J=2.7 Hz, 1H), 8.44 (t, J=5.6 Hz, 1H), 7.78 (d, J=8.4 Hz, 2H), 7.76-7.72 (m, 1H), 7.54 (d, J=8.2 Hz, 2H), 7.52-7.48 (m, 1H), 7.37-7.27 (m, 2H), 7.03 (d, J=7.8 Hz, 1H), 6.86 (d, J=2.5 Hz, 1H), 4.73-4.61 (m, 1H), 3.46-3.37 (m, 2H), 2.47 (t, J=7.0 Hz, 2H), 2.39-2.23 (m, 1H), 2.14-1.92 (m, 2H), 1.20-1.13 (m, 1H); (M+1): 446.2.

Provenance & Evidence