Lithium hydroxide, monohydrate → HCID 46203918, compound

Participants

Reaction Steps

To a stirred solution of {6-fluoro-4-[4-(piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester (0.100 g, 0.17 mmol) in tetrahydrofuran (6 mL) was added a solution of lithium hydroxide monohydrate (0.035 g, 0.83 mmol) in water (1.5 mL) and the reaction mixture was stirred for 48 hours at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water (8 mL) and washed with ethyl acetate (2×5 mL). The aqueous layer was acidified with an aqueous solution of hydrochloric acid (1 N), then extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.050 g (52%) of {6-fluoro-4-[4-(piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.13-8.17 (m, 1 H), 8.12 (s, 1 H), 7.99 (d, J=8.0 Hz, 2 H), 7.93-7.98 (m, 1 H), 7.89 (d, J=8.0 Hz, 2 H), 7.67 (s, 1 H), 7.57 (td, J=8.6, 2.0 Hz, 1 H), 3.76 (s, 2 H), 2.89 (br. s, 4 H), 2.76 (br. s, 4 H). MS cald. for C23H21FN2O5S [M+] 456, obsd. 456.9.

Provenance & Evidence