Hydrogen Peroxide → HCID 66713059, compound

HRID 1468985Notes

Reaction equation

HRID 1468985 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:47].S([O-])([O-])=O.[Na+].[Na+].[Na+].[Na+]>O1CCCC1.ClCCl>[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

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 853005Di-tert-butyl N,N-DiisopropylphosphoramiditeHCID 23618808HCID 23618808, compoundHCID 66713252HCID 66713252, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 66713059HCID 66713059, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 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 bissulfite (1.1 g) were added. The resulting mixture was diluted with dichloromethane 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. washthe organic layer was washed with water extensively until the water layer
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0-66% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-3620cc482de649f1a919141353c502a4
Source dataset
uspto-grants-2015_04
Patent number
US09006247B2

Reaction notes

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