Lithium hydroxide, monohydrate → {6-Fluoro-3-methyl-4-[4-(toluene-2-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid

Participants

Reaction Steps

To a solution of {6-fluoro-3-methyl-4-[4-(toluene-2-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (20 mg, 0.04 mmol) in THF (5 mL) was added a solution of lithium hydroxide monohydrate (19.3 mg, 0.46 mmol) in water (1 mL) at room temperature. The resulting clear solution was stirred for 15 hours and then THF was removed under vacuum. Water (30 mL) was added and the mixture was acidified with 1.0N hydrochloric acid. The resulting solids were collected by filtration and washed with water and hexanes. After drying in air, {6-fluoro-3-methyl-4-[4-(toluene-2-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid (10 mg, 52%) was isolated as off-white solid. 1H NMR (400 MHz, Methanol-d4) δ ppm 8.27 (d, J=7.9 Hz, 1 H), 8.04 (d, J=8.2 Hz, 2 H), 7.88 (dd, J=8.8, 6.0 Hz, 1 H), 7.81 (s, 1 H), 7.61 (t, J=7.5 Hz, 1 H), 7.48-7.55 (m, 1 H), 7.48 (d, J=8.2 Hz, 2 H), 7.40 (d, J=7.5 Hz, 1 H), 7.22 (td, J=8.8, 2.1 Hz, 1H), 6.65 (dd, J=11.2, 2.1 Hz, 1 H), 3.86 (s, 2 H), 2.52 (s, 3 H), 2.11 (s, 3 H). HRMS (ES−) calcd. for C26H20FO4S [(M−H)−] 447.1072, obsd. 447.1070.

Provenance & Evidence