Lithium hydroxide, monohydrate → HCID 46206859, compound

Participants

Reaction Steps

To a stirred solution of 4-[4-(3-ethoxycarbonylmethyl-7-fluoro-naphthalene-1-carbonyl)-benzenesulfonyl]-piperazine-1-carboxylic acid ethyl ester (0.110 g, 0.20 mmol) in tetrahydrofuran (12 mL) was added a solution of lithium hydroxide monohydrate (0.042 g, 0.99 mmol) in water (3 mL) and the reaction mixture was stirred for 14 hours at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water (6 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 layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 0.058 (56%) of 4-[4-(3-carboxymethyl-7-fluoro-naphthalene-1-carbonyl)-benzenesulfonyl]-piperazine-1-carboxylic acid ethyl ester as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51 (br. s, 1 H), 8.10-8.20 (m, 2H), 8.00 (d, J=8.3 Hz, 2 H), 7.90 (d, J=8.3 Hz, 2 H), 7.82-7.88 (m, 1 H), 7.72 (s, 1 H), 7.57 (td, J=8.7, 2.2 Hz, 1 H), 3.99 (q, J=6.9 Hz, 2 H), 3.82 (s, 2 H), 3.46 (br. s, 4 H), 2.96 (br. s, 4 H), 1.13 (t, J=6.9 Hz, 3 H). MS cald. for C26H25FN2O7S ([M+H]+) 529, obsd. 529.3.

Provenance & Evidence