Réaction #48445

Équation de réaction

(3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-ethylazepan-2-one

N,N-diisopropylethylamine

diphenyl N-cyanocarbonimidate

→

title compound

Rendement 80.0%

Phenyl N′-cyano-N-[(3R,6S)-6-(2,3-difluorophenyl)-1-ethyl-2-oxoazepan-3-yl]imidocarbamate

Rendement 80.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe reaction was quenched with 0.5N NaOH
2. 2
   Lavagethe organic layer washed with water and brine
3. 3
   ExtractionThe combined aqueous layers were extracted with EtOAc
4. 4
   AutreThe combined organics were dried
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutrePurification by silica gel chromatography (EtOAc/hexanes)

Mode opératoire

A solution of (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-ethylazepan-2-one (135 mg, 0.503 mmol) in dichloromethane was treated N,N-diisopropylethylamine (65 mg, 0.503 mmol) and diphenyl N-cyanocarbonimidate (204 mg, 0.855 mmol). After 5 h, the reaction was quenched with 0.5N NaOH and the organic layer washed with water and brine. The combined aqueous layers were extracted with EtOAc. The combined organics were dried, filtered and concentrated. Purification by silica gel chromatography (EtOAc/hexanes) gave the title compound (166 mg). MS 413.3 (M+1).

Source