Hydrogen Peroxide → HCID 44828616, compound

HRID 2047450Notes

Reaction equation

HRID 2047450 reaction equation
C([C@@H]1COC(=O)N1C([C@@H:16]1[C@@H:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:19][N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:17]1)=O)C1C=CC=CC=1.[OH:35]O.[OH-].[Li+].C1[CH2:43][O:42]CC1>O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[C:31]([O:30][C:28]([N:18]1[CH2:19][C@H:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C@@H:16]([C:43]([OH:42])=[O:35])[CH2:17]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67232594HCID 67232594, compound

Product 1

HCID 44828616HCID 44828616, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a mixed solution of tert-butyl (3R,4S)-3-{[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl}-4-(4-fluorophenyl)pyrrolidine-1-carboxylate (0.32 g) obtained in step 2 in THF (14.4 mL) and water (4.8 mL) were added 30% aqueous hydrogen peroxide (939 μL) and 4N aqueous lithium hydroxide solution (518 μL) at 0° C., and the mixture was stirred at room temperature for 8 hr. The reaction mixture was diluted with aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed with water and extracted with 0.5N aqueous sodium hydroxide solution. The extract was washed with ethyl acetate, acidified with 10% aqueous citric acid solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure to give (3R,4S)-1-(tert-butoxycarbonyl)-4-(4-fluorophenyl)pyrrolidine-3-carboxylic acid (0.185 g, 88%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. extractionextracted with 0.5N aqueous sodium hydroxide solution
  4. washThe extract was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. customdried
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8246a21cc4f44264b919c0e74b0e4750
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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