(1,1'-Biphenyl)-4-sulphonyl chloride → [5-(Biphenyl-4-sulfonylamino)-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-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (199 mg, 0.72 mmol) and biphenyl-4-sulfonyl chloride (217 mg, 0.86 mmol) in dry tetrahydrofuran (10 mL) was added diisopropylethylamine (186 mg, 1.44 mmol) at 0° C. The reaction mixture was stirred at room temperature for 12 hours, and then concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, and evaporated in vacuo. Column chromatography (silica gel, 100-200 mesh, 10-15% ethyl acetate in hexane) gave [5-(biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester. MS cald. for C28H31NO5S 493, obsd. 494 [(M+H)+].

Provenance & Evidence