Dichloromethane → (R)-5-Fluoro-3-(1-(2-(3-fluoroazetidin-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 crude (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-fluoroazetidine-1-carboxylate (32-5, 25.8 mg, 0.035 mmol) to DCM (277 μl) and TFA (69.4 μl). After 15 min, diluted with 1 mL MeOH, filtered through Celite and concentrated in vacuo. Dissolved in 2 mL DMSO and purified by reverse-phase HPLC (C18 column, 5-60% 0.1% TFA/CH3CN:0.1% TFA/H2O) to give 32-6 as a white solid. 1H NMR δ (ppm) (CH3OH-d4): 8.22 (1H, s), 7.80 (1H, d, J=7.86 Hz), 7.75 (1H, d, J=5.61 Hz), 7.62 (1H, t, J=7.61 Hz), 7.56-7.44 (2H, m), 7.06 (1H, d, J=9.97 Hz), 5.49 (1H, d, J=6.64 Hz), 5.12-4.90 (2H, m), 4.81-4.61 (2H, m), 1.95 (3H, d, J=7.03 Hz). HRMS C20H18F2N5O4S2 [M+H] calc: 494.0763, obs: 494.0754.

Provenance & Evidence