Lithium hydroxide, monohydrate → HCID 71604241, compound

Participants

Reaction Steps

To a solution of {4-[1-(2-amino-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (178 mg, 0.367 mmol) in THF 8.0 mL) was added a solution of lithium hydroxide monohydrate (176 mg, 7.35 mmol) in water (2.0 mL) at room temperature. The resulting solution was stirred for 15 hours under nitrogen. The solvent was removed under vacuum and the aqueous solution was diluted with water and slowly neutralized with 1.0 N HCl until the pH was between 5 and 6. The resulting precipitated solids were collected by filtration and washed with water and hexanes. After drying in the air, {4-[1-(2-amino-phenylmethane-sulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid (159 mg, 92%) was isolated as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.44 (br. s, 1H), 7.86 (dd, J=8.85, 6.59 Hz, 1H), 7.61 (s, 1H), 7.31 (t, J=7.91 Hz, 1H), 7.18 (d, J=7.35 Hz, 1H), 6.99-7.12 (m, 2H), 6.68-6.78 (m, 1H), 6.53-6.67 (m, 1H), 5.14 (br. s, 2H), 4.28-4.51 (m, 4H), 3.76 (d, J=10.93 Hz, 2H), 3.61 (br. s, 5H), 2.41 (br. s, 3H), 1.66 (d, J=11.49 Hz, 2H). MS cald. for C25H26FN2O4S [(M−H)−] 469, obsd. 469.1.

Provenance & Evidence