Hydrogen Peroxide → HCID 66713059, compound

HRID 1478146Notes

Reaction equation

HRID 1478146 reaction equation
[OH:1][CH2:2][C:3]([CH3:20])([CH3:19])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17].C(N(C(C)C)[P:25]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(C)C.N1C=NN=N1.OO.S(=O)(=O)(O)[O-:47].[Na+]>O1CCCC1>[P:25]([O:1][CH2:2][C:3]([CH3:20])([CH3:19])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:13])(=[O:14])[NH2:15])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:47]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 516919Sodium BisulfateHCID 853005Di-tert-butyl N,N-DiisopropylphosphoramiditeHCID 66713252HCID 66713252, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 66713059HCID 66713059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 4A (540 mg) in tetrahydrofuran (5 ml) was added di-tert-butyl diisopropylphosphoramidite (0.84 ml) and 0.45 M 1H-tetrazole (7.91 ml) at 0° C. The mixture was stirred at room temperature for 1.5 hours and cooled to 0° C. 30% Hydrogen peroxide (0.82 ml) was added. The mixture was stirred at room temperature for 30 minutes. Ice water and sodium bisulfate (1.1 g) were added. The resulting mixture was diluted with dicholormethane and the organic layer was washed with water extensively until the water layer became pH neutral. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography, eluting with 0-66% ethyl acetate in dichloromethane to provide the title compound.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. additionThe resulting mixture was diluted with dicholormethane
  4. washthe organic layer was washed with water extensively until the water layer
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with 0-66% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-62d0cb29f3d44607a9744acc094bd448
Source dataset
uspto-grants-2016_08
Patent number
US09403822B2

Reaction notes

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