Hydrogen Peroxide → HCID 86726357, compound

HRID 629755Notes

Reaction equation

HRID 629755 reaction equation
[N:1]([C@@H:4]([C@H:19]([C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=1)[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:5](N1[C@@H](C2C=CC=CC=2)COC1=O)=[O:6])=[N+:2]=[N-:3].OO.[Li+].[OH-].S([O-])([O-])=[O:40].[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[N:1]([C@@H:4]([C@H:19]([C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=1)[C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:5]([OH:40])=[O:6])=[N+:2]=[N-:3]

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 86726358HCID 86726358, compound

Product 1

HCID 86726357HCID 86726357, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (4S)-3-[(2S,3S)-2-azido-3-(3,5-difluorophenyl)-3-(4-fluorophenyl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one (3.1 g, 6.7 mmol) in 45 mL of THF and 15 mL of water was cooled to 0° C. in an ice-water bath. To the stirred solution was added hydrogen peroxide (2.7 mL of a 30% solution in water, 27 mmol) and LiOH (0.32 g, 13 mmol), and the mixture was stirred at 0° C. for 45 min. The reaction was quenched by the addition of a solution of sodium sulfite (3.4 g, 27 mmol) in 20 mL of water, followed by 67 mL of a 0.5 M solution of aqueous NaHCO3 (33 mmol). The stirred mixture was warmed to ambient temperature and most of the THF was removed in vacuo. The aqueous mixture was extracted with two portions of CH2Cl2 to remove the chiral auxiliary. The aqueous phase was then acidified to pH 1 with the addition of 6 N HCl and extracted with two portions of EtOAc. The combined EtOAc layers were dried (MgSO4), filtered, and the solvent was removed in vacuo to give a gum.

Workup

  1. customwas removed in vacuo
  2. extractionThe aqueous mixture was extracted with two portions of CH2Cl2
  3. customto remove the chiral auxiliary
  4. additionThe aqueous phase was then acidified to pH 1 with the addition of 6 N HCl
  5. extractionextracted with two portions of EtOAc
  6. dry with materialThe combined EtOAc layers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customto give a gum

Sources & evidence

ORD record
ord-9f325c4e83ad4ea6b9c87281355ff7e6
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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