Acetic Acid → HCID 13271641, compound

HRID 358145Notes

Reaction equation

HRID 358145 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[N:26]=[CH:27][NH:28][C:29]=1[C:30]([NH2:32])=[O:31])(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[C@@H:6]1([O:24][C:25]2[N:26]=[CH:27][NH:28][C:29]=2[C:30]([NH2:32])=[O:31])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13271636HCID 13271636, compound

Product 1

HCID 13271641HCID 13271641, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 457 mg of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy-1H-imidazole-5-carboxamide in 30 ml of dry methanol was added 270 mg of 95% sodium methoxide. The reaction mixture was stirred for 20 minutes at room temperature and 0.33 ml of acetic acid was added. Chromatographical purification on LH-20 (product of Pharmacia A/S) in methanol of the residue which was obtained after evaporation of the reaction mixture under reduced pressure, gave 260 mg of 4-β-D-glucopyranosyloxy-1H-imidazole-5-carboxamide which was crystallized with acetone. m.p. 167° C. (dec.)

Workup

  1. customChromatographical purification on LH-20 (product of Pharmacia A/S) in methanol of the residue which
  2. customwas obtained
  3. customafter evaporation of the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-21952899a89548dfb8da6c72975190f6
Source dataset
uspto-grants-1984_08
Patent number
US04464531

Reaction notes

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