Hydrogen Peroxide → HCID 490266, compound

HRID 345755Notes

Reaction equation

HRID 345755 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:13]([C@@H:14]3[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]3[OH:16])[CH:12]=[N:11][C:10]=2[C:23]#[N:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:25]O>>[C:1]1([C:7]#[C:8][C:9]2[N:13]([C@@H:14]3[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]3[OH:16])[CH:12]=[N:11][C:10]=2[C:23]([NH2:24])=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 784Hydrogen PeroxideHCID 14556097HCID 14556097, compound

Product 1

HCID 490266HCID 490266, compoundYield 79.6%

Procedure

To a solution of 10 mg (0.03 mmol) of 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carbonitrile dissolved in 4 ml of aqueous ammoniamethanol (1:1 V/V) was added 0.2 ml of hydrogen peroxide, and the reaction was carried out with stirring at room temperature for 30 minutes. After the reaction, the solvent was evaporated and the residue was adsorbed onto a silica gel column (1.8×35 cm) and eluted with a 5-20% ethanol-chloroform solvent mixture to obtain 8.4. mg of 5-(phenylethyn-1-yl)-1-β-D-ribofuranosylimidazole-4-carboxamide (yield: 79.6%).

Workup

  1. customAfter the reaction
  2. customthe solvent was evaporated
  3. washeluted with a 5-20% ethanol-chloroform solvent mixture
  4. customto obtain 8.4

Sources & evidence

ORD record
ord-5c864f4203c1402196d026b4b4093ec8
Source dataset
uspto-grants-1991_10
Patent number
US05059590

Reaction notes

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