Triethylamine → tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-({[2-(trimethylsilyl)ethoxy]carbonyl}amino)-1,4-oxazepane-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid (1.0 g) in toluene (10 mL) were added diphenylphosphoryl azide (0.828 mL) and triethylamine (0.536 mL) at room temperature, and the mixture was stirred at 90° C. for 30 min. To the reaction mixture was added 2-(trimethylsilyl)ethanol (0.727 mL) at 90° C., and the mixture was stirred at 90° C. for 2 hr. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (0.67 g).

Provenance & Evidence