tert-Butanol → Methyl 2-{[(tert-butoxycarbonyl)amino]methyl}-3-(4-chlorophenyl)propanoate

Participants

Reaction Steps

Diphenylphosphoryl azide (2.1 g, 76 mmol) was added to a solution of 3-(4-chlorobenzyl)-4-methoxy-4-oxobutanoic acid (1.6 g, 6.4 mmol) and triethylamine (“TEA”; 0.97 g, 9.58 mmol) in t-BuOH (40 mL). The reaction mixture was then heated to reflux and stirred for 6 hours. The reaction was then cooled to room temperature and concentrated to an oil. Purification by column chromatography (9:1 to 5:1 hexane:EtOAc) gave methyl 3-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)propanoate (0.64 g, 31%).

Provenance & Evidence