Reaktion #1109800

Reaktionsgleichung

2-(trimethylsilyl)ethanol

(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

diphenylphosphoryl azide

triethylamine

→

title compound

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

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 90° C. for 2 hr
2. 2
   WaschenThe diluted solution was washed with distilled water and brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Vorschrift

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).

Quelle