Ethyl Acetate → N-(5S)-[3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

HRID 1108574Notes

Reaction equation

HRID 1108574 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[C:19](=[O:25])[CH2:18]3)=[C:13]([F:26])[CH:12]=2)[CH2:6]1)=[N+]=[N-].[C:27](OCC)(=[O:29])[CH3:28]>CN(C=O)C>[F:26][C:13]1[CH:12]=[C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][NH:1][C:27](=[O:29])[CH3:28])[O:9][C:8]2=[O:10])[CH:16]=[CH:15][C:14]=1[N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[C:19](=[O:25])[CH2:18]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 53831456(5R)-5-azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one

Product 1

HCID 21968862N-(5S)-[3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(5R)-5-Azidomethyl-3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl-}phenyl)oxazolidin-2-one (750 mg) was dissolved in a mixture of DMF (5 ml) and ethyl acetate (10 ml), and the solution purged with argon. Palladium (10% on carbon, 150 mg) was added, followed by acetic anhydride (0.4 ml) and the mixture stirred at ambient temperature under hydrogen confined in a balloon for 2 hours. The mixture was filtered through celite, evaporated to dryness, and chromatographed on silica, using as eluant a gradient increasing in polarity from 0 to 10% methanol in dichloromethane. Relevant fractions were combined and evaporated, and the residue purified by crystallisation from acetonitrile to give N-(5S)-[3-(3-fluoro-4-{4-ethyl-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (145 mg).

Workup

  1. customthe solution purged with argon
  2. additionPalladium (10% on carbon, 150 mg) was added
  3. filtrationThe mixture was filtered through celite
  4. customevaporated to dryness
  5. customchromatographed on silica
  6. temperaturea gradient increasing in polarity from 0 to 10% methanol in dichloromethane
  7. customevaporated
  8. customthe residue purified by crystallisation from acetonitrile

Sources & evidence

ORD record
ord-57e33a7062cc4cd5afc86bead539681d
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

Loading…