Reaktion #85654

Reaktionsgleichung

1-chloro-N,N,2-trimethylprop-1-en-1-amine

(R)-2-((S)-2-oxooxazolidin-4-yl)propanoic acid

N,O-dimethylhydroxylamine

pyridine

→

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

Ausbeute 195.4%

Lösungsmittel

dichloromethane

DCM

DCM

water

sodium bicarbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice bath was removed
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITwas continued for ˜1 hr
5. 5
   workup.STIRRINGstirred for ˜15 min
6. 6
   ExtraktionThe separated aqueous layer was extracted with DCM (1×)
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated under reduced pressure

Vorschrift

To a mixture of (R)-2-((S)-2-oxooxazolidin-4-yl)propanoic acid (1.1 g, 6.91 mmol) in DCM (20 mL) was added 1-chloro-N,N,2-trimethylprop-1-en-1-amine (1.385 g, 10.37 mmol) at 0° C. The ice bath was removed and the mixture was stirred for 30 min at ambient temperature. A mixture of N,O-dimethylhydroxylamine (1.011 g, 10.37 mmol) and pyridine (1.677 mL, 20.74 mmol) in DCM (20 mL) was added and stirring was continued for ˜1 hr. The mixture was diluted with water (˜2 mL) and saturated sodium bicarbonate solution (˜2 mL) and stirred for ˜15 min. The mixture was diluted with dichloromethane (˜30 mL). The separated aqueous layer was extracted with DCM (1×), the organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure providing crude (R)—N-methoxy-N-methyl-2-((S)-2-oxooxazolidin-4-yl)propanamide (2.73 g) as an orange oil which was directly used without further purification. MS m/z 203.1 (M+H)+; Rt-0.36 min.

Quelle