Lithium hydroxide, monohydrate → HCID 71604109, compound

Participants

Reaction Steps

To a stirred solution of {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid methyl ester (115 mg, 0.23 mmol) in THF (6 mL) was added a solution of lithium hydroxide monohydrate (50 mg, 1.2 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 {4-[1-(2,4-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-naphthalen-2-yl}-acetic acid (100 mg, 89%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.35 (br s, 1H), 8.02 (d, J=8.3 Hz, 1H), 7.96-8.00 (m, 2H), 7.87-7.95 (m, 1H), 7.68-7.73 (m, 2H), 7.34-7.44 (m, 2H), 3.87 (d, J=12.2 Hz, 2H), 3.72 (s, 2H), 3.04 (t, J=11.5 Hz, 2H), 1.89-1.96 (m, 2H), 1.67-1.78 (m, 2H); MS cald. for C23H19Cl2FNO4S [(M−H)−]: 494, obsd. 494.3.

Provenance & Evidence