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

HRID 2299025Notes

Reaction equation

HRID 2299025 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][N:14]=[N+:15]=[N-:16])[N:10]=[CH:9]1.[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[C:29]#[CH:30]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH2:13][N:14]2[CH:30]=[C:29]([C:28]([O:32][CH2:33][CH3:34])=[O:31])[N:16]=[N:15]2)[N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 12182Ethyl propiolate2×HCID 57003668N-[(5S)-3-(3-Fluoro-4-(4-azidomethylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-yl-methyl]acetamide

Product 1

HCID 18340190N-[(5S)3-(3-Fluoro-4-(4-(4-ethoxycarbonyl-1,2,3-triazol-1-yl)methylimidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamideYield 72.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7198908fcd054c7ebe6c740d71420f6e
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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