Triphenylphosphine → Triphenylphosphine Oxide

Participants

Reaction Steps

To (S)-3-(2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (194 mg, 0.50 mmol), 2-isoquinolin-4-yl-ethanol (108 mg, 0.625 mmol), triphenyl phosphine (197 mg, 0.75 mmol) in THF(5 mL) was added diethyl azodicarboxylate (133 μL, 0.85 mmol). After 16 h the solvent was removed under reduced pressure, the residue was chromatographed on silica gel 20% THF in dichloromethane to give (S)-3-[2-(2-isoquinolin-4-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a colorless foam (394 mg, contaminated with triphenyl phosphine oxide). MS (APCI) m/z 544.1 (M+1).

Provenance & Evidence