tert-Butanol → Tert-butyl 4'-methoxy-4-biphenylcarbamate

Participants

Reaction Steps

A mixture of 4′-methoxy-biphenyl-4-carboxylic acid (10.68 g, 46.8 mmol), prepared in the previous step, triethylamine (6.52 mL, 46.8 mmol) and diphenylphosphoryl azide (10.08 mL, 46.8 mmol) in 200 mL of tert-butyl alcohol was refluxed under nitrogen for 7 h and then stood overnight at room temperature. The tert-butyl alcohol was removed under reduced pressure. The residue was dissolved in methylene chloride, extracted with 1 N HCl, 1 N NaOH, dried (MgSO4) and the solvent removed under reduced pressure to give tert-butyl 4′-methoxy-4-biphenylcarbamate (11.1 g, 79%) as a white solid, mp 142-147° C., MS (ESI) m/z 300 [M+H]+. Elemental Analysis for C18H21NO3: Calc'd: C, 72.22; H, 7.07; N, 4.68; Found: C, 71.25; H, 6.92; N, 4.74.

Provenance & Evidence