Hydrogen Peroxide → HCID 86718429, compound

HRID 2273308Notes

Reaction equation

HRID 2273308 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)=[N:2]1.N1C=NN=N1.C(N(C(C)C)[P:30]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])(C)C.OO.S([O-])([O-])(=[O:48])=S.[Na+].[Na+]>C1COCC1>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[C:9]([CH2:11][O:12][P:30](=[O:48])([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40])[N:10]=2)=[N:2]1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 853005Di-tert-butyl N,N-DiisopropylphosphoramiditeHCID 86718427HCID 86718427, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 86718429HCID 86718429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in step (3) (1.61 g) and 1H-tetrazole (760 mg) were dissolved in THF (20 ml), di-tert-butyl N,N-diisopropylphosphoramidite (2.45 ml) was added at room temperature under stirring, and stirring was conducted for 2 hours. This reaction solution was cooled to 0° C., 30% aqueous hydrogen peroxide (0.250 ml) was added, and stirring was conducted for 14 hours while the temperature was gradually returned to room temperature. A saturated aqueous sodium thiosulfate solution was added to the reaction solution to stop the reaction, and the reaction mixture was extracted with ethyl acetate. The extract liquid was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→50%) using a silica gel column (trade name: SNAP Cartridge KP-Sil 100 g, manufactured by Biotage Ltd.) to give the title compound (2.21 g).

Workup

  1. stirringstirring
  2. stirringstirring
  3. waitwas conducted for 14 hours while the temperature
  4. customwas gradually returned to room temperature
  5. customthe reaction
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. washThe extract liquid was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→50%)

Sources & evidence

ORD record
ord-15d8fe603a464b73a558c3daf1aeb972
Source dataset
uspto-grants-2015_09
Patent number
US09120835B2

Reaction notes

Loading…