Dichloromethane → (R)-5-Fluoro-3-(1-(2-(3-hydroxyazetidin-3-yl)phenyl)ethyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Participants

Reaction Steps

In a 1 dram vial, added (R)-tert-butyl 3-(2-(1-(6-(N-(2,4-dimethoxybenzyl)-N-(1,2,4-thiadiazol-5-yl)sulfamoyl)-5-fluoro-2-oxobenzo[d]oxazol-3(2H)-yl)ethyl)phenyl)-3-hydroxyazetidine-1-carboxylate (32-3, 60 mg, 0.081 mmol) to DCM (647 μl) and TFA (162 μl). After 15 min, diluted with 1 mL MeOH, filtered through Celite, purified by reverse-phase HPLC (20 min run, 5-60% 0.1% TFA/CH3CN:0.1% TFA/H2O) to give 32-4 as a white solid. 1H NMR δ (ppm) (CH3OH-d4): 8.21 (1H, s), 7.83 (1H, d, J=7.64 Hz), 7.71 (1H, d, J=5.61 Hz), 7.54-7.41 (2H, m), 7.27 (1H, d, J=7.61 Hz), 7.00 (1H, d, J=10.04 Hz), 5.52 (1H, dt, J=13.86, 6.77 Hz), 4.42 (2H, dd, J=10.60, 3.89 Hz), 4.14 (2H, dd, J=10.77, 3.87 Hz), 1.95 (3H, d, J=6.97 Hz). HRMS C20H19FN505S2 [M+H] calc: 492.0806, obs: 492.0796.

Provenance & Evidence