Sodium Hydroxide → HCID 178484859, compound

Participants

Reaction Steps

To a suspension of 1 g (2.96 mmol) of trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide in 12 mL of toluene were added 0.9 ml (6.04 mmol, 2 eq) of bromo-acetic acid tert-butyl ester, 100 mg (0.3mmol, 0.1 eq) of tetra-N-butylammonium hydrogensulfate and 12 mL of 50% aqueous NaOH. The mixture was stirred at 500 for 1 h. The organic phase was dissolved in EtOAc, dried over Na2SO4, and the solvent evaporated. Column chromatography on silica gel gave 1.3 g (97%) of trans-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester as an off-white solid, MS: 469 (M+NH4+).

Provenance & Evidence