Ammonia methanol → HCID 178476362, compound

HRID 568571Notes

Reaction equation

HRID 568571 reaction equation
[C:1]([C:3]1[NH:4][CH:5]=[N+:6]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[C:7]=1[O-:8])#[N:2].N.CO>CO>[C:1]([C:3]1[NH:4][CH:5]=[N+:6]([C@@H:9]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[C@@H:15]([OH:16])[C@H:10]2[OH:11])[C:7]=1[O-:8])#[N:2].[C:1]([C:3]1[NH:4][CH:5]=[N+:6]([C@@H:9]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:15]([OH:16])[C@H:10]2[OH:11])[C:7]=1[O-:8])#[N:2]

Participants

5

Reactant 2

HCID 21705897Ammonia methanolHCID 178476361HCID 178476361, compound

Product 2

HCID 178476362HCID 178476362, compoundHCID 178510665HCID 178510665, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 184 mg of 4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazolium-5-olate and 1 ml of dry methanol was added 15 ml of 15% (W/W) ammonia/methanol solution under cooling, and the mixture was stirred for two hours at the same temperature. Evaporation of the reaction mixture in vacuo gave a residue, which was purified by column chromatography on reversed phase silica gel [Merck RP-8 eluted with aqueous 10% methanol containing acetic acid (1%)] to give 100 mg of 4-cyano-1-(5-O-acetyl-β-D-ribofuranosyl)imidazolium-5-olate and 32 mg of 4-cyano-1-β-D-ribofuranosylimidazolium-5-olate, which was identified with the authentic sample of Example 2.

Workup

  1. temperatureunder cooling
  2. customEvaporation of the reaction mixture in vacuo
  3. customgave a residue, which
  4. customwas purified by column chromatography on reversed phase silica gel [Merck RP-8 eluted with aqueous 10% methanol containing acetic acid (1%)]

Sources & evidence

ORD record
ord-94638986ab1b4602bceebb396d9f9870
Source dataset
uspto-grants-1988_03
Patent number
US04728729

Reaction notes

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