Hydrogen Peroxide → HCID 68734733, compound

HRID 79496Notes

Reaction equation

HRID 79496 reaction equation
OO.O[Li].O.C([C@@H]1COC(=O)N1[C:19](=[O:43])[C@H:20]([C@H:29]1[N:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:32]([CH3:42])([CH3:41])[CH2:31][CH2:30]1)[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)C1C=CC=CC=1.[O-:44]S([O-])=O.[Na+:48].[Na+]>C1COCC1.O>[Na+:48].[C:37]([O:36][C:34]([N:33]1[C:32]([CH3:42])([CH3:41])[CH2:31][CH2:30][C@H:29]1[C@H:20]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)[C:19]([O-:43])=[O:44])=[O:35])([CH3:38])([CH3:39])[CH3:40]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 68759221(s)-Tert-butyl 5-((s)-2-((r)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-chloro-3-fluorophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate

Product 1

HCID 68734733HCID 68734733, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

30% H2O2 (0.159 mL, 1.65 mmol) was added to a solution of LiOH—H2O (0.055 g, 1.32 mmol) in 2:1 THF:H2O (40 mL). The mixture was stirred for 20 minutes and then cooled to 0° C. A solution of (S)-tert-butyl 5-((S)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(4-chloro-3-fluorophenyl)-2-oxoethyl)-2,2-dimethylpyrrolidine-1-carboxylate (0.360 g, 0.660 mmol) in THF (3 mL) was next added slowly. Upon completion of the addition, the reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was then recooled to 0° C., and 1M Na2SO3 (4 mL) was added. The reaction was stirred for 10 minutes at 0° C. and then warmed to room temperature and stirred for an additional 10 minutes. The reaction was then concentrated in vacuo to remove THF, and the resulting mixture was washed with EtOAc. The organic fraction was then dried over sodium sulfate, filtered and concentrated to give (S)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)-2-(4-chloro-3-fluorophenyl)acetic acid sodium salt (0.24 g, 94%) as a powder. MS ESI (+) m/z 386 detected.

Workup

  1. additionUpon completion of the addition
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. customwas then recooled to 0° C.
  5. stirringThe reaction was stirred for 10 minutes at 0° C.
  6. temperaturewarmed to room temperature
  7. stirringstirred for an additional 10 minutes
  8. concentrationThe reaction was then concentrated in vacuo
  9. customto remove THF
  10. washthe resulting mixture was washed with EtOAc
  11. dry with materialThe organic fraction was then dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-6e988e20df6745629183dd3b2ebff314
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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