Hydrogen Peroxide → HCID 178507181, compound

HRID 623327Notes

Reaction equation

HRID 623327 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[OH:20]O>C(O)(=O)C.[Pd].C(O)C>[C@@H:1]1([N:10]2[C:19]3[C:13](=[C:14]([N+:16]([O-:20])=[CH:17][N:18]=3)[NH2:15])[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

6

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 60961Adenosine

Product 1

HCID 178507181HCID 178507181, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Twenty grams of adenosine (commercialized by Sigma-Aldrich Corporation, St. Louis, Mo. USA, Product code: A9251-25G) was dispersed in one liter of acetic acid, admixed with 100 mL of hydrogen peroxide solution, and stirred at ambient temperature for five days. To the resulting solution was added five grams of 5% palladium on carbon, commercialized by Kawaken Fine Chemicals Co., Ltd, Tokyo, Japan, followed by decomposing an excessive amount of hydrogen peroxide, filtering the resultant to remove palladium carbon, drying the resulting solution in vacuo, adding ethanol to unstiffen the formed crystals, and filtering the resultant to obtain a crude crystalline adenosine N1-oxide. The crude crystals were dissolved by heating in two liters of ethanol, filtered, and ice chilled for crystallization, followed by repeating the recrystallization step twice to obtain eight grams of adenosine N1-oxide with a purity of 99.5%.

Workup

  1. filtrationfiltering the resultant
  2. customto remove palladium carbon
  3. customdrying the resulting solution in vacuo
  4. additionadding ethanol
  5. filtrationfiltering the resultant
  6. customto obtain a crude crystalline adenosine N1-oxide
  7. dissolutionThe crude crystals were dissolved
  8. filtrationfiltered
  9. temperatureice chilled for crystallization
  10. customthe recrystallization step twice

Sources & evidence

ORD record
ord-08be6ac03d714254b0303bbc09bd48d8
Source dataset
uspto-grants-2016_04
Patent number
US09301968B2

Reaction notes

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