HCID 15549557, compound → HCID 86584039, compound

HRID 651217Notes

Reaction equation

HRID 651217 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][C@H:27]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])[O:26][C:25]3=[O:34])=[CH:20][C:19]=2[F:35])[CH2:14][CH2:13]1)(=[O:11])=[O:10])#[N:2].C1C=C([O:42]O)C(C(O)=O)=C(C(O)=O)C=1>CO>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:28][C@@H:27]([CH2:29][NH+:30]([O-:42])[C:31](=[O:33])[CH3:32])[O:26][C:25]3=[O:34])=[CH:20][C:19]=2[F:35])[CH2:16][CH2:17]1)(=[O:11])=[O:10])#[N:2]

Participants

4

Reactant 2

HCID 15549557HCID 15549557, compoundHCID 198097063-Hydroperoxyphthalic acid

Product 1

HCID 86584039HCID 86584039, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-N-[[3-[4-[4-[(2-cyanophenyl)sulfonyl]-1-piperazinyl]-3-fluorophenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (VIII-G, R1=COCH3, R9=2-cyanophenyl, X1=F, X2=H) (0.5 g) is suspended in 10 mL of methanol. Monoperoxyphthalic acid, magnesium salt hexahydrate (80% pure, 0.616 g) is added and the reaction mixture is stirred at room temperature for 2 hours. The reaction is concentrated and the resulting oil is chromatographed on silica gel using 7% methanol (saturated with ammonia) in chloroform as eluent to afford 0.33 g of the N-oxide.

Workup

  1. concentrationThe reaction is concentrated
  2. customthe resulting oil is chromatographed on silica gel using 7% methanol (saturated with ammonia) in chloroform as eluent

Sources & evidence

ORD record
ord-87055680f18e4701871ce25cfde06974
Source dataset
uspto-grants-2001_08
Patent number
US06277985B1

Reaction notes

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