Triphenylphosphine → (R)-3-(1-(Isoquinolin-8-yl)ethyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(2,4-dimethoxybenzyl)-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (100 mg, 0.214 mmol) and (S)-1-(isoquinolin-8-yl)ethanol (74.3 mg, 0.429 mmol) in THF (1072 μl) at 0° C. was treated with PS-triphenylphosphine (112 mg, 0.429 mmol) (0.233 g resin-bound PPh3, 1.84 mmol PPh3/g of resin), and (E)-di-tert-butyl diazene-1,2-dicarboxylate (99 mg, 0.429 mmol). Reaction mixtured was monitored at 0° C. After stirring at 0° C. for 2 h, the reaction was filtered and concentrated in vacuo. Residue was dissolved in 1 mL of DCM and treated with 0.25 mL of TFA. After stirring at RT for 30 minutes, the solvent and TFA were removed in vacuo. Purified by reverse phase chromatography (10-95% MeCN in water w/0.1% TFA, C18 column) to yield 14-7. 1H NMR δ (ppm)(CH3OH-d4): 9.86 (1H, s), 8.61 (1H, d, J=6.42 Hz), 8.47 (2H, dd, J=14.05, 6.52 Hz), 8.32-8.24 (2H, m), 8.14 (1H, s), 7.64-7.57 (2H, m), 7.29 (1H, d, J=8.39 Hz), 6.64-6.55 (1H, m), 2.15 (3H, d, J=7.05 Hz). HRMS [M+H]C20H15N5O4S2 calc'd 454.0638. Found 454.0633.

Provenance & Evidence