Reacción #85655

Ecuación de reacción

(R)—N-methoxy-N-methyl-2-((S)-2-oxooxazolidin-4-yl)propanamide

(bromomethyl)benzene

sodium hydride

→

(R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)-N-methoxy-N-methylpropanamide

Rendimiento 97.4%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ice bath was removed
2. 2
   workup.ADDITIONThe mixture were diluted carefully with water and ethyl acetate
3. 3
   OtroThe aqueous layer was separated
4. 4
   Extracciónextracted with ethyl acetate (1×)
5. 5
   SecadoThe combined organic layers were dried over sodium sulfate
6. 6
   Filtraciónfiltered off
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by column chromatography [SiO2, 80 g, EtOAc/heptane=5/95 to 75/25]

Procedimiento

To a mixture of crude (R)—N-methoxy-N-methyl-2-((S)-2-oxooxazolidin-4-yl)propanamide (1.3 g, 6.43 mmol) and (bromomethyl)benzene (1.30 mL, 11.4 mmol) in THF (25 mL) was added slowly sodium hydride (60% wt.; 0.643 g) at 0° C. [Caution: gas development!]. The ice bath was removed and the mixture was stirred for ˜2 hr. The mixture were diluted carefully with water and ethyl acetate. The reaction was repeated on the same scale and the mixtures were combined. The aqueous layer was separated and extracted with ethyl acetate (1×). The combined organic layers were dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 80 g, EtOAc/heptane=5/95 to 75/25] to provide (R)-2-((S)-3-benzyl-2-oxooxazolidin-4-yl)-N-methoxy-N-methylpropanamide (1.83 g) as a slightly yellow oil, which contained also N-methoxy-N-methylisobutyramide. MS m/z 293.7 (M+H)+; Rt-0.64 min.

Fuente