Hydrochloric Acid → HCID 86681675, compound

Participants

Reaction Steps

To a solution of (S)-4-(2-(2-(6-(N-(tert-butoxycarbonyl)methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (0.200 g, 0.254 mmol) in DCM (10 ml) cooled to 0° C., HCl 4M in THF (0.634 ml, 2.54 mmol) was added, and the mixture was warmed to room temperature and stirred for 48 hours. A white solid precipitated. The precipitate was collected by filtration and washed with DCM affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(6-(methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetoxy)ethyl)pyridine 1-oxide (0.140 g, 0.203 mmol, 80% yield). MS/ESI+ 688.1 [MH]+; [αD]=−31.04, c=0.46, MeOH; 1H NMR (300 MHz, DMSO-d6) δ ppm 9.66 (br. s., 1H), 8.43 (s, 2H), 7.25 (d, 1H), 7.19 (d, 1H), 7.15 (d, 1H), 7.08 (d, 1H), 7.05 (dd, 1H), 6.96 (dd, 1H), 7.07 (t, 1H), 6.04 (dd, 1H), 4.82 (d, 1H), 4.70 (d, 1H), 3.92 (d, 2H), 3.40 (dd, 1H), 3.22 (dd, 1H), 2.99 (s, 3H), 1.07-1.41 (m, 1H), 0.48-0.70 (m, 2H), 0.25-0.44 (m, 2H).

Provenance & Evidence