Réaction #9178

Équation de réaction

bis-(2-oxo-3-oxazolidinyl)-phosphorylchloride

triethylamine

O-benzylhydroxylamine hydrochloride

8-bromo octanoic acid

→

8-bromo-octanoic acid benzyloxyamide

Rendement 78.0%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGStirring
2. 2
   ExtractionThe solution was extracted twice with 150 ml each of 1M aqueous hydrochloric acid and twice with 150 ml each of 1M aqueous sodium bicarbonate
3. 3
   AutreThe organic solvent was removed i

Mode opératoire

In an ice bath, 14 ml triethylamine was added to a suspension of 3.2 g (20 mmol) O-benzylhydroxylamine hydrochloride in 150 ml dichloromethane. Stirring was continued until the solution became clear. Then, 4.5 g (20 mmol) 8-bromo octanoic acid was added, followed by 5.6 g (22 mmol) bis-(2-oxo-3-oxazolidinyl)-phosphorylchloride. Stirring was continued at ambient temperature for 18 h. The solution was extracted twice with 150 ml each of 1M aqueous hydrochloric acid and twice with 150 ml each of 1M aqueous sodium bicarbonate. The organic solvent was removed i. vac. to give 5.1 g (78%) of 8-bromo-octanoic acid benzyloxyamide as a colorless oil. MS: 330 (M+H+)

Source