Diisopropylethylamine → [5-(3,5-Bis-trifluoromethyl-benzenesulfonylamino)-3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester

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Reaction Steps

To a solution of (5-amino-3-chloro-2-fluoro-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (125.0 mg, 0.38 mmol) and 3,5-di-(trifluoromethyl)benzene-1-sulfonyl chloride (0.117 g, 0.38 mmol) in dry tetrahydrofuran (5 mL) was added diisopropylethylamine (0.2 mL, 0.94 mmol) at 0° C. under nitrogen. After 2 hours of stirring at room temperature, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The collected organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Column chromatography (silica gel, 100-200 mesh, 5% 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 tert-butyl ester (163.2 mg, 71%). MS cald. for C24H23ClF7NO5S 605, obsd. 604 [(M+H)+].

Provenance & Evidence