Eperezolid → (S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]-methyl]acetamide N-oxide

HRID 1060976Notes

Reaction equation

HRID 1060976 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:18]2[CH2:22][C@H:21]([CH2:23][NH:24][C:25](=[O:27])[CH3:26])[O:20][C:19]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15][OH:16])[CH2:10][CH2:9]1.C1C=C([O:35]O)C(C(O)=O)=C(C(O)=O)C=1>CO>[F:1][C:2]1[CH:3]=[C:4]([N:18]2[CH2:22][C@@H:21]([CH2:23][NH+:24]([O-:35])[C:25](=[O:27])[CH3:26])[O:20][C:19]2=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15][OH:16])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 73214EperezolidHCID 198097063-Hydroperoxyphthalic acid

Product 1

HCID 86584035(S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]-methyl]acetamide N-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

(S)-N-[[3-[3-Fluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide (VIII-A, R1=COCH3, R2=H, X1=F, X2=H) (11.8 g) is dissolved in 200 mL of methanol. Monoperoxyphthalic acid, magnesium salt hexahydrate (80% pure, 18.5 g) is added and the resulting suspension is stirred at 25° C. for two hours. The reaction is filtered and the filtrate is concentrated to afford a white solid. This solid is chromatographed on silica gel using 20% methanol in chloroform as eluent to afford the N-oxide. Lyophilization of this material affords the purified product as a hydrate (9.5 g).

Workup

  1. filtrationThe reaction is filtered
  2. concentrationthe filtrate is concentrated
  3. customto afford a white solid
  4. customThis solid is chromatographed on silica gel using 20% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-c5fd4ac6777743028848d6cd9c0a3c34
Source dataset
uspto-grants-2003_02
Patent number
US06525193B2

Reaction notes

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