Lithium hydroxide, monohydrate → HCID 46202302, compound

Participants

Reaction Steps

To a stirred solution of {6-fluoro-4-[4-(4-methyl-piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid ethyl ester (0.05 g, 0.10 mmol) in tetrahydrofuran (6 mL) was added a solution of lithium hydroxide monohydrate (0.021 g, 0.50 mmol) in water (1.5 mL) and the reaction mixture was stirred for 48 hours at room temperature. The solvents were distilled off under reduced pressure, then the residue was diluted with water (4 mL) and washed with ethyl acetate (2×3 mL) to remove unwanted organic products. The aqueous layer was separated and acidified to pH ˜3-4 with a 1.0 N aqueous solution of hydrochloric acid. The resulting mixture was extracted with ethyl acetate (2×10 mL). The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 0.020 g (42%) of {6-fluoro-4-[4-(4-methyl-piperazine-1-sulfonyl)-benzoyl]-naphthalen-2-yl}-acetic acid as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.09-8.19 (m, 2 H), 7.84-8.05 (m, 5 H), 7.71 (s, 1 H), 7.48-7.61 (m, 1 H), 3.81 (s, 2 H), 2.97 (br. s, 4 H), 2.38 (br. s, 4 H), 2.15 (s, 3 H). MS cald. for C24H23FN2O5S ([M+H]+) 471, obsd. 471.3.

Provenance & Evidence