HCID 15549553, compound → HCID 86585621, compound

HRID 651215Notes

Reaction equation

HRID 651215 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:19]2[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:5]=[C:6]([F:18])[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:36]O)C(C(O)=O)=C(C(O)=O)C=1>CO>[F:18][C:6]1[CH:5]=[C:4]([N:19]2[CH2:23][C@@H:22]([CH2:24][NH+:25]([O-:36])[C:26](=[O:28])[CH3:27])[O:21][C:20]2=[O:29])[CH:3]=[C:2]([F:1])[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 15549553HCID 15549553, compoundHCID 198097063-Hydroperoxyphthalic acid2×

Product 1

HCID 86585621HCID 86585621, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

(S)-N-[[3-[3,5-Difluoro-4-[4-(hydroxyacetyl)-1-piperazinyl]-phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide (VIII-A, R1=COCH3, R2=H, X1=X2=F) (0.13 g) is dissolved in 5 mL of methanol. Monoperoxyphthalic acid, magnesium salt hexahydrate (80% pure, 0.2 g) is added and the resulting suspension is stirred at 25° C. for 72 hours. An additional 0.2 g of monoperoxyphthalic acid is added and the reaction is stirred an additional 48 hours. The reaction mixture is filtered and the filtrate is concentrated to afford a light-yellow oil. This material is chromatographed on silica gel using 20% methanol (saturated with ammonia) in chloroform as eluent to afford 55 mg of the N-oxide.

Workup

  1. stirringthe reaction is stirred an additional 48 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated
  4. customto afford a light-yellow oil
  5. customThis material is chromatographed on silica gel using 20% methanol (saturated with ammonia) in chloroform as eluent

Sources & evidence

ORD record
ord-d141250f41214a36afd301e050da8be9
Source dataset
uspto-grants-2001_08
Patent number
US06277985B1

Reaction notes

Loading…