Sodium methanolate methanol → HCID 178510665, compound

HRID 568570Notes

Reaction equation

HRID 568570 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(=O)C)[C@@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[C:7]=1[O-:8])#[N:2].CO.C[O-].[Na+]>CO>[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

4

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 178476361HCID 178476361, compound

Product 1

HCID 178510665HCID 178510665, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 6.921 g of 4-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazolium-5-olate and 50 ml of dry methanol was added 20.37 g of 25% (W/W) sodium methoxide methanol solution under ice-cooling. The reaction mixture was stirred for ten minutes at the same temperature and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography on reversed phase silica gel [Merck RP-8 eluted with 1% acetic acid solution] to give 4.21 g of 4-cyano-1-β-D-ribofuranosylimidazolium-5-olate.

Workup

  1. temperaturecooling
  2. concentrationconcentrated to dryness in vacuo
  3. customThe resulting residue was purified by column chromatography on reversed phase silica gel [Merck RP-8 eluted with 1% acetic acid solution]

Sources & evidence

ORD record
ord-71b1a1719c1a435182a63ae6426b2977
Source dataset
uspto-grants-1988_03
Patent number
US04728729

Reaction notes

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