N-(3-mercaptophenyl)methanesulfonamide → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(methylsulfonamido) phenylthio)carbonyloxy)ethyl)pyridine 1-oxide

Participants

Reaction Steps

To a suspension of N-(3-mercaptophenyl)methanesulfonamide (97 mg, 0.478 mmol) in DCM (15 ml), under nitrogen atmosphere, (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-nitrophenoxy)-carbonyloxy)ethyl)pyridine 1-oxide (prepared with an analogous procedure to that described in Scheme 3, Step 1) (200 mg, 0.342 mmol), and DMAP (20.87 mg, 0.171 mmol) were added, and the reaction mixture was stirred at RT for 3 hours. The organic solution was washed with K2CO3 dil. aq., dried over Na2SO4, filtered and evaporated. The crude was triturated with EtOH affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((3-(methylsulfonamido) phenylthio)carbonyloxy)ethyl)pyridine 1-oxide (162.9 mg, 0.251 mmol, 73.4% yield, MS/ESI+ 649.04 [MH]+, [αD]=−93.81, c=0.53 in DCM).

Provenance & Evidence