Hydrogen Peroxide → HCID 86726355, compound

HRID 629752Notes

Reaction equation

HRID 629752 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:10][C:11](N2[C@H](C3C=CC=CC=3)COC2=O)=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1.OO.[Li+].[OH-].S([O-])([O-])=[O:37].[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[F:8][C:6]1[CH:5]=[C:4]([C@H:9]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:10][C:11]([OH:12])=[O:37])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 86726353HCID 86726353, compound

Product 1

HCID 86726355HCID 86726355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (4R)-3-[(3S)-3-(3,5-difluorophenyl)-3-(4-fluorophenyl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one (7.3 g, 17 mmol) in 90 mL of THF and 30 mL of water was cooled to 0° C. in an ice-water bath. To the solution was added hydrogen peroxide (7.0 mL of a 30% solution in water, 69 mmol) and LiOH (0.83 gg, 35 mmol). After 45 min, a solution of sodium sulfite (8.7 g, 69 mmol) in 30 mL of water was added, followed by 170 mL of a 0.5 M solution of aqueous NaHCO3 (86 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 solid.

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 solid

Sources & evidence

ORD record
ord-7bac49c7f5a74f30a635bba6b3cba979
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

Loading…