Lithium hydroxide, monohydrate → HCID 22275143, compound

Participants

Reaction Steps

A solution of ethyl-4-[2-(1-{[(4-chlorophenyl)sulfonyl]-2,5-difluoroanilino}ethyl)phenoxy]butanoate (1.16 g, 2.2 mmol) in THF (5.2 mL), methanol (1.7 mL) and H2O (1.7 mL) was treated with LiOH.H2O (91 mg, 2.2 mmol) at 25° C. for 3 h. The reaction was then quenched with 1 N HCl solution. The aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with H2O and sat. NaCl aqueous solution, then dried over MgSO4. Concentration and chromatography afforded the desired product (457 mg, 41%) as white crystal: m.p. 141.0-142.0° C.; Rf 0.14 (10:10, hexane-ethyl acetate); 1H NMR (CDCl3, 300 MHz) δ 11.08 (br s, 1H), 7.62 (d, 2H, J=8.4 Hz), 7.35 (d, 2H, J=8.7 Hz), 7.16 (t, 1H, J=7.5 Hz), 6.38-6.93 (m, 6H), 6.03 (br s, 1H), 4.06 (m, 2H), 2.70 (t, 2H, J=7.0 Hz), 2.17 (m, 2H), 1.57 (d, 3H, J=6.9 Hz); LCMS 3.05 min, m/z 527.2 (C24H22ClF2NO5S requires 509.95).

Provenance & Evidence