[O:1]=[C:2]1[NH:6][C@@H:5]([C@@H:7]([CH3:11])[C:8]([OH:10])=O)[CH2:4][O:3]1.ClC(N(C)C)=C(C)C.[CH3:20][NH:21][O:22][CH3:23].N1C=CC=CC=1>C(Cl)Cl.O.C(=O)(O)[O-].[Na+]>[CH3:23][O:22][N:21]([CH3:20])[C:8](=[O:10])[C@@H:7]([C@H:5]1[CH2:4][O:3][C:2](=[O:1])[NH:6]1)[CH3:11]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.
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