Ethyl Acetate → [4-(2-Amino-4-benzoylaminophenoxy)phenyl]carbamic acid tert-butyl ester

Participants

Reaction Steps

The product from Example 252a (1.50 g, 3.3 mmol), Fe powder (0.78 g, 13.4 mmol) and NH4Cl (0.71 g, 13.4 mmol) in a mixture of THF (7.5 mL) and H2O (3 mL) was gradually heated to reflux and refluxed for 19 hours. The reaction mixture was portioned between EtOAc and 10% NaHCO3 and then filtered (through celite). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound which was purified by column chromatography on silica gel eluting with 1:1 n-hexane/EtOAc to give the title compound as a yellow foam (1.32 g, 94%).

Provenance & Evidence