Hydrogen Peroxide → HCID 490266, compound

HRID 893705Notes

Reaction equation

HRID 893705 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-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-ethanol-chloroform solvent mixture

Sources & evidence

ORD record
ord-9adcef798034412c96873d84a2809a31
Source dataset
uspto-grants-1992_06
Patent number
US05126361

Reaction notes

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