Lithium hydroxide, monohydrate → HCID 71604045, compound

Participants

Reaction Steps

To a stirred solution of {6-fluoro-4-[1-(3-methanesulfonyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (115 mg, 0.22 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (46 mg, 1.1 mmol) in water (1.5 mL) and the reaction mixture was stirred for 24 h at RT. The reaction mixture was concentrated under reduced pressure and washed with diethyl ether (3×5 mL). The washings were discarded. Water (5 mL) was added to the residue, and the mixture acidified (pH ˜2-3) with an aqueous solution of hydrochloric acid (2 N) and extracted with ethyl acetate (3×5 mL). The combined organic extracts were dried over Na2SO4 and evaporated under reduced pressure to give {6-fluoro-4-[1-(3-methanesulfonyl-benzenesulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid (90 mg, 80%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.35 (br s, 1H), 8.34 (d, J=7.8 Hz, 1H), 8.23 (s, 1H), 8.18 (d, J=7.8 Hz, 1H), 7.98-8.04 (m, 1H), 7.95 (dd, J=9.3, 6.4 Hz, 1H), 7.86 (d, J=12.7 Hz, 1H), 7.69 (s, 1H), 7.35-7.41 (m, 2H), 3.87 (d, J=10.3 Hz, 2H), 3.71 (s, 2H), 3.39 (s, 3H), 2.66 (d, J=10.3 Hz, 2H), 1.89-1.96 (m, 2H), 1.73-1.83 (m, 1H); MS cald. for C24H25FNO6S2 [(M−H)−]: 506, obsd. 506.2.

Provenance & Evidence