Water → HCID 86749481, compound

HRID 2393876Notes

Reaction equation

HRID 2393876 reaction equation
[CH3:1][C:2]1(Br)[O:19][C@H:18]([C:20]([OH:22])=[O:21])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:9][C:10](=[O:12])[CH3:11])[C@H:3]1[O:4][C:5](=[O:7])[CH3:6].[N-:24]=[N+:25]=[N-:26].[Na+].O>CN(C)C=O>[CH3:1][C:2]1([N:24]=[N+:25]=[N-:26])[O:19][C@H:18]([C:20]([OH:22])=[O:21])[C@@H:13]([O:14][C:15](=[O:17])[CH3:16])[C@H:8]([O:9][C:10](=[O:12])[CH3:11])[C@H:3]1[O:4][C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 131720831HCID 131720831, compound

Product 1

HCID 86749481HCID 86749481, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 2,3,4,-tri-O-acetylglucopyranuronosyl bromide (7.94 g, 20 mmol) was dissolved in 250 ml of dimethylformamide and 2.6 g, that is 40 mmol of sodium azide was added. The mixture was stirred at room temperature for 24 hours and then poured into 500 ml of H2O. The organic soluble material was extracted three times with 150 ml ethyl acetate. The combined ethyl acetate extracts were washed twice with 100 ml H2O, brine, dried over MgSO4, and concentrated to dryness. The residue was recrystallized from ethanol to yield 5.46 g (76%) of methyl 2,3,4,-tri-O-acetylglucopyranuronosyl azide. Methyl 2,3,4,-tri-O-acetylglucopyranuronosyl azide had the melting point of 152°-154°.

Workup

  1. additionwas added
  2. extractionThe organic soluble material was extracted three times with 150 ml ethyl acetate
  3. washThe combined ethyl acetate extracts were washed twice with 100 ml H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f2f574ae1add4522800279adfe45e908
Source dataset
uspto-grants-1998_09
Patent number
US05808111

Reaction notes

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