Triphenylphosphine → 3-(4-Amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-n-methyl-succinamic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 0.167 g (0.972 mmol) 2-quinolin-5-yl-ethanol, 0.48 g (1.94 mmol) triphenyl phosphine, and 0.392 g (0.972 mmol) 3-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester was stirred in 25 mL THF at room temperature under a nitrogen atmosphere. 0.31 mL (1.94 mmol) diethyl azodicarboxylate was added dropwise and the mixture stirred 18 h. TLC anaylsis indicated complete reaction. The solvent was evaporated under reduced pressure and the residue purified on silica eluting with 1:1 hexanes:EtOAc to EtOAc yielding 0.23 g (43%) of 3-(4-amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester as a colorless foam. MS (APCI) m/z 559 (M+1).

Provenance & Evidence