Ethyl propiolate → N-[(5S)3-(3-Fluoro-4-(4-(4-ethoxycarbonyl-1,2,3-triazol-1-yl)methylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

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Reaction Steps

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.

Provenance & Evidence