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Hydrogen Peroxide → HCID 86584037, compound

HRID 1058115
Notes
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Reaction equation

HRID 1058115 reaction equation
OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:6].[F:16][C:17]1[CH:18]=[C:19]([N:33]2[CH2:37][C@H:36]([CH2:38][NH:39][C:40](=[O:42])[CH3:41])[O:35][C:34]2=[O:43])[CH:20]=[CH:21][C:22]=1[N:23]1[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]1>C(Cl)Cl>[F:16][C:17]1[CH:18]=[C:19]([N:33]2[CH2:37][C@@H:36]([CH2:38][NH+:39]([O-:6])[C:40](=[O:42])[CH3:41])[O:35][C:34]2=[O:43])[CH:20]=[CH:21][C:22]=1[N:23]1[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 10431934N-[[(5S)-3-[3-Fluoro-4-[4-(methylsulfonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 86584037HCID 86584037, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Pertrifluoroacetic acid is prepared in situ by the addition of 30% H2O2 solution (0.15 mL) to trifluoroacetic anhydride (0.45 mL) in 5 mL of methylene chloride at 0° C. This solution is stirred at 0° C. for ten minutes, at 25° C. for 30 minutes and then cooled back to 0° C. (S)-N-[[3-[3-fluoro-4-[4-(methylsulfonyl)-1-piperazinyl]phenyl]-2-oxo-5-oxazolidinyl]-methyl]acetamide (VIII-G, R1=COCH3, R9=CH3, X1F, X2=H) (0.207 g) is added and the reaction is stirred at 25° C. for 30 minutes and then concentrated. The residue is chromatographed on silica gel using 10% methanol (saturated with ammonia) in chloroform as the eluent to afford 0.14 g of the N-oxide as a hydrate.

Workup

  1. additionis added
  2. stirringthe reaction is stirred at 25° C. for 30 minutes
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel using 10% methanol (saturated with ammonia) in chloroform as the eluent

Sources & evidence

ORD record
ord-0f054964b4f448089e7319695348f5ee
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06515135B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes