Sodium Azide → HCID 2725013, compound

HRID 2182823Notes

Reaction equation

HRID 2182823 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[N:25]=[N+:26]=[N-:27])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

Product 1

HCID 2725013HCID 2725013, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Five grams (12.2 millimoles) of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was dissolved in 120 ml of DMF, and 15.8 g (243 millimoles) of sodium azide was added with agitation. The reaction mixture was agitated at room temperature for a day and a night while shielded from light. The reaction mixture was added dropwise to 1,000 ml of ice water with agitation, and the insoluble material was extracted using 900 ml of methylene chloride. The organic phase was washed with ice water and dried using anhydrous sodium sulfate. The drying agent was separated by filtration, and the solvent was completely removed by distillation under reduced pressure. The pale yellow solid obtained was washed using diethyl ether, dried and recrystallized from 2-propanol to obtain 3.30 g (79% yield) of 2,3,4,6-tetra-O-acetyl-β-glucopyranosyl azide in the form of white needle shaped crystals. The physical properties of the product are shown below.

Workup

  1. extractionthe insoluble material was extracted
  2. washThe organic phase was washed with ice water
  3. customdried
  4. customThe drying agent was separated by filtration
  5. customthe solvent was completely removed by distillation under reduced pressure
  6. customThe pale yellow solid obtained
  7. washwas washed
  8. customdried
  9. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-101df707ac3a4432b1cfa9b1c304286a
Source dataset
uspto-grants-2005_05
Patent number
US06897326B2

Reaction notes

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