Hydrogen Peroxide → HCID 66845563, compound

HRID 1480558Notes

Reaction equation

HRID 1480558 reaction equation
[OH2:1].[OH-].[Li+].O.OO.C([C@@H]1COC(=O)N1C(=O)[C@H:21]([C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([F:32])[CH:23]=1)C1C=CC=CC=1.C1[CH2:50][O:49]CC1>>[C:41]([O:40][C:38]([N:34]1[CH2:35][CH2:36][CH2:37][C@H:33]1[C@H:21]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:30])([F:29])[F:31])=[C:24]([F:32])[CH:23]=1)[C:50]([OH:49])=[O:1])=[O:39])([CH3:43])([CH3:42])[CH3:44]

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 168937Lithium hydroxide, monohydrateHCID 86650048HCID 86650048, compound

Product 1

HCID 66845563HCID 66845563, compoundYield 3.52%

Procedure

Lithium hydroxide hydrate (0.22 g, 5.24 mmol) was dissolved in THF (20 mL) and water (10 mL) and then treated with hydrogen peroxide (35 wt %) (1.00 g, 10.3 mmol). After stirring at ambient temperature for 30 minutes, the solution was cooled to 0° C. (S)-tert-Butyl 2-((S)-2-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-2-oxoethyl)pyrrolidine-1-carboxylate (1.44 g, 2.62 mmol) was added as a solution in THF (10 mL). The mixture was stirred at 0° C. for 1 hour and then warmed to ambient temperature overnight. The reaction was quenched with 10% K2SO3 (4 mL) and saturated NaHCO3 (4 mL) and stirred at ambient temperature for 20 minutes. The reaction was concentrated in vacuo, and the aqueous phase was washed with ether (3×50 mL). The aqueous phase was diluted with ethyl acetate (50 mL), cooled to 0° C., and acidified with 1N HCl to a pH of 3. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with 1N HCl (2×20 mL), dried over Na2SO4 and then concentrated in vacuo (0.036 g, 3.52% yield). MS (APCI−) [M−H] 389.8.

Workup

  1. stirringThe mixture was stirred at 0° C. for 1 hour
  2. temperaturewarmed to ambient temperature overnight
  3. customThe reaction was quenched with 10% K2SO3 (4 mL) and saturated NaHCO3 (4 mL)
  4. stirringstirred at ambient temperature for 20 minutes
  5. concentrationThe reaction was concentrated in vacuo
  6. washthe aqueous phase was washed with ether (3×50 mL)
  7. additionThe aqueous phase was diluted with ethyl acetate (50 mL)
  8. temperaturecooled to 0° C.
  9. customThe organic phase was separated
  10. extractionthe aqueous phase was extracted with ethyl acetate (3×50 mL)
  11. washThe combined organic phase was washed with 1N HCl (2×20 mL)
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated in vacuo (0.036 g, 3.52% yield)

Sources & evidence

ORD record
ord-49a7841c22014132849b1409160aefcd
Source dataset
uspto-grants-2016_08
Patent number
US09409886B2

Reaction notes

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