反应详情

N-[(5S)-3-(3-Fluoro-4-(4-azidomethylimidazol-1-yl)phenyl )-2-oxooxazolidin-5-yl-methyl]acetamide (200 mg, 0.54 mM) and ethyl propiolate (79 mg, 0.81 mM) were dissolved in acetonitrile (10 ml) and heated under reflux for 3 hours. Further ethyl propio late (79 mg) was added, and heting continued for a total of 7 hours. Solvent was evaporated, the residue dissolved in the minimum volume of dichloromethane, and chromatographed on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the title product (184 mg), containing about 10% of the 5-ethoxycarbonyl isomer.

1. temperatureheated
2. temperatureunder reflux for 3 hours
3. customheting continued for a total of 7 hours
4. customSolvent was evaporated
5. dissolutionthe residue dissolved in the minimum volume of dichloromethane
6. customchromatographed on a 10 g silica Mega Bond Elut® column
7. washeluting with
8. temperaturea gradient increasing in polarity from 0 to 10% methanol in dichloromethane
9. customevaporated