Sulfuric Acid → N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)methanesulfonamide

Participants

Reaction Steps

To a solution of crude S-3-(cyclopropylmethoxy)-4-(methylsulfonamido)-phenyl O-ethyl carbonodithioate (prepared as described in Step 7, 0.903 g, 2.497 mmol) in MeOH (15 ml), KOH (0.392 g, 6.99 mmol) was added followed by NaBH4 (0.071 g, 1.873 mmol), and the mixture was stirred at RT for 1 hour. NaBH4 (0.047 g, 1.249 mmol) was freshly added, and the mixture was stirred at RT for 1 hour. Then the mixture was acidified with 10% H2SO4 (until effervescence ceased). The residue was portioned between EtOAc and water, and the organic layer was washed with water, dried over na2SO4 and evaporated. The residue was purified by flash chromatography on silica gel cartridge (DCM:EtOAc=80:20) affording N-(2-(cyclopropylmethoxy)-4-mercaptophenyl)methanesulfonamide (0.222 g, 0.812 mmol, 32.5% yield, MS/ESI+ 295.9 [MNa]+).

Provenance & Evidence