Lithium hydroxide, monohydrate → HCID 71604112, compound

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Reaction Steps

To a clear, almost colorless solution of {4-[1-(2-chloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (108 mg, 0.23 mmol) in THF (8.0 mL) was added a solution of lithium hydroxide monohydrate (106 mg, 4.4 mmol) in water (2.0 mL) The mixture was heated with a heat gun to give a clear solution. The resulting solution was stirred for 15 hours at room temperature. The solvent was removed under vacuum. The residue was diluted with water (˜20 mL) and the mixture was neutralized with 1.0 N HCl. The precipitated white solids were collected by filtration and washed with water and hexanes. After air drying, {4-[1-(2-chloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (93 mg, 87%) was isolated as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.42 (br. s, 1H), 8.07 (d, J=7.53 Hz, 2H), 783-7.96 (m, 1H), 7.65-7.82 (m, 3H), 7.56-7.64 (m, 1H), 7.28-7.40 (m, 1H), 3.91 (d, J=11.29 Hz, 4H), 3.76 (br. s, 3H), 3.05 (br. s, 2H), 2.36 (s, 3H), 1.68 (d, J=12.3 Hz, 2H). MS cald. for C24H24ClFNO4S [(M+H)+] 476, obsd. 476.1.

Provenance & Evidence