Methanol → HCID 46174383, compound

Participants

Reaction Steps

To a stirred solution of [5-(3,5-bis-trifluoromethyl-benzenesulfonylamino)-3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester (163.4 mg, 0.27 mmol) in tetrahydrofuran (4 mL) were added an aqueous (2 mL) solution of lithium hydroxide (0.036 g, 0.87 mmol) and methanol (1 mL) at room temperature and the resulting reaction mixture was stirred for 2 hours. The solvent was removed under reduced pressure. The residue was diluted with water (15 mL) and acidified with dilute hydrochloric acid, which resulted in the formation of a precipitate. The resulting mixture was extracted with ethyl acetate (15 mL×3). The combined organic layers was washed with water (15 mL×3), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Column chromatography (silica gel, 100-200 mesh, 50% ethyl acetate in hexane) gave [5-(3,5-bis-trifluoromethyl-benzenesulfonylamino)-3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid (130.4 mg, 88%). MS cald. for C20H15ClF7NO5S 549, obsd. 548 (ESI+) [(M−H)+].

Provenance & Evidence