Reaktion #85655

Reaktionsgleichung

(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

Ausbeute 97.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle