Hydrogen Peroxide → HCID 63362718, compound

HRID 83511Notes

Reaction equation

HRID 83511 reaction equation
O.[OH-].[Li+].OO.C([C@@H]1COC(=O)N1[C:19]([CH:21]1[CH2:26][N:25]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=2[O:36][CH3:37])[C:24](=[O:38])[CH2:23][CH2:22]1)=[O:20])C1C=CC=CC=1.S([O-])(O)=[O:40].[Na+]>O.O1CCCC1>[CH3:37][O:36][C:29]1[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:28]=1[CH2:27][N:25]1[C:24](=[O:38])[CH2:23][CH2:22][CH:21]([C:19]([OH:20])=[O:40])[CH2:26]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 23665763Sodium BisulfiteHCID 712878795-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(2,4-dimethoxybenzyl)piperidin-2-one

Product 1

HCID 63362718HCID 63362718, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium hydroxide monohydrate (316 mg) in water (10 ml) was added dropwise a 30 wt % aqueous solution of hydrogen peroxide (1.8 ml) under ice-cooling and the mixture was stirred for 10 minutes. To this reaction solution was added tetrahydrofuran (10 ml), and then a solution of the low-polarity component of 5-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-1-(2,4-dimethoxybenzyl)piperidin-2-one (3.37 g) in tetrahydrofuran (20 ml) was added dropwise thereto, and the mixture was stirred for additional 1 hour. To this reaction solution was added an aqueous solution of sodium hydrogen sulfite (1.81 g) was added dropwise, and then the mixture was warmed to room temperature, and stirred for 30 minutes. This mixed solution was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue was added ethyl acetate, and the mixture was stirred at room temperature. The insoluble substance was collected by filtration, and dried under reduced pressure to give the titled compound (1.36 g). An analysis of this solid by HPLC analysis condition 2 showed that an isomer with shorter retention time was a main product.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for additional 1 hour
  3. additionwas added dropwise
  4. stirringstirred for 30 minutes
  5. extractionThis mixed solution was extracted with ethyl acetate
  6. washthe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionTo the resulting residue was added ethyl acetate
  10. stirringthe mixture was stirred at room temperature
  11. filtrationThe insoluble substance was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-b835b698947d4185adccc02a7f8ddba1
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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