Ethanethiol → N-(4-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-2-ethylsulfanyl-ethanesulfonamide

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Reaction Steps

A 0° C. solution of ethanethiol (0.1 mL, 1.35 mmol) in THF (5 mL) is treated with NaH (81 mg, 2 mmol, 60% in mineral oil) and stirred for 10 m. The mixture is added a solution of N-(4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-2-chloro-ethanesulfonamide (500 mg, 1 mmol) in THF (10 mL), warmed to RT, and stirred overnight. The reaction is concentrated, dissolved in CH2Cl2, and washed with 0.2 N HCl. The organic layer is concentrated and chromatographed (0%-20% EtOA/Hex) to give the title compound (270 mg, 51%).

Provenance & Evidence