Hydrogen Peroxide → HCID 11822201, compound

HRID 469703Notes

Reaction equation

HRID 469703 reaction equation
[CH3:1][O:2][C:3]1([O:18][CH3:19])[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:6](=[O:17])[CH:5]=[CH:4]1.[OH:20]O.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1([O:18][CH3:19])[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:6](=[O:17])[CH:5]2[CH:4]1[O:20]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 11086797HCID 11086797, compound

Product 1

HCID 11822201HCID 11822201, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 3 (3.4 g, 12.7 mol) in tetrahydrofuran (93 mL) was cooled in an ice bath. To the stirring solution, in drop-wise fashion, was added hydrogen peroxide (30% aq., 22 mL) and aqueous sodium hydroxide (1M, 61 mL) in tandem using 2 separate addition funnels and utilizing a Claisen adapter. The reaction mixture was stirred for 30 minutes in the ice bath and then for 5 hours at room temperature. The flask was cooled in an ice bath and the peroxide was carefully quenched with manganese dioxide. After filtration of the mixture over a small bed of silica gel followed by rinsing of the silica gel with ethyl acetate, the mixture was washed with brine. The organics were then dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting oil was treated with pentane to precipitate an off white solid after solvent evaporation yielding 2 g (56%) of compound (4). 1H NMR indicated 20% starting material in the mixture, which was easily removed in the next step (treatment with TFA). The 1H NMR of the product was consistent with that reported in the literature (Synthesis 1998, 775).

Workup

  1. customseparate
  2. additionaddition funnels
  3. waitfor 5 hours at room temperature
  4. temperatureThe flask was cooled in an ice bath
  5. customthe peroxide was carefully quenched with manganese dioxide
  6. filtrationAfter filtration of the mixture over a small bed of silica gel
  7. washby rinsing of the silica gel with ethyl acetate
  8. washthe mixture was washed with brine
  9. dry with materialThe organics were then dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. additionThe resulting oil was treated with pentane
  13. customto precipitate an off white solid
  14. customafter solvent evaporation

Sources & evidence

ORD record
ord-c7b243102b584cfe9be0eff9c49bfe8c
Source dataset
uspto-grants-2014_01
Patent number
US08629164B2

Reaction notes

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