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

HRID 1108583Notes

Reaction equation

HRID 1108583 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][CH2:24][O:25][CH3:26])[C:19](=[O:27])[CH2:18]3)=[C:13]([F:28])[CH:12]=2)[CH2:6]1)=[N+]=[N-].[C:29](OCC)(=[O:31])[CH3:30]>>[F:28][C:13]1[CH:12]=[C:11]([N:7]2[CH2:6][C@H:5]([CH2:4][NH:1][C:29](=[O:31])[CH3:30])[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][CH2:24][O:25][CH3:26])[C:19](=[O:27])[CH2:18]1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 53675945(5R)-5-Azidomethyl-3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one

Product 1

HCID 21968861N-(5S)-[3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide

Procedure

(5R)-5-Azidomethyl-3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)oxazolidin-2-one (750 mg) was dissolved in ethyl acetate (15 ml), and the solution purged with argon. Palladium (10% on carbon, 150 mg) was added, followed by acetic anhydride (0.36 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 5% methanol in dichloromethane. Relevant fractions were combined and evaporated, to give N-(5S)-[3-(3-fluoro-4-{4-(2-methoxyethyl)-3-oxopiperazin-1-yl}phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (228 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 5% methanol in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-539afb452dde4f178dff9ae31004d543
Source dataset
uspto-grants-2000_05
Patent number
US06069145

Reaction notes

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