Sodium Azide → HCID 14866070, compound

HRID 1378528Notes

Reaction equation

HRID 1378528 reaction equation
[CH3:1][C:2]([CH2:4][C@@H:5]([C@@H:7]([CH2:9]OS(C1C=CC(C)=CC=1)(=O)=O)[OH:8])[OH:6])=[O:3].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[CH3:1][C:2]([CH2:4][C@@H:5]([C@@H:7]([CH2:9][N:21]=[N+:22]=[N-:23])[OH:8])[OH:6])=[O:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 54385761HCID 54385761, compound

Product 1

HCID 14866070HCID 14866070, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl-2-deoxy-5-O-tosyl-D-ribose (13.6 g, 45 mmol) in DMF (250 mL) was added sodium azide (4.4 g, 67 mmol). The mixture was refluxed for 4 hours, cooled to room temperature, quenched with ice water (1.5 mL), and extracted with ethyl-acetate. The extract was washed with water, dried, and concentrated to give an oil (6.2 g, 86% yield). NMR

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customquenched with ice water (1.5 mL)
  3. extractionextracted with ethyl-acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-640c990167894c0dbacd344488b6fd9c
Source dataset
uspto-grants-1997_09
Patent number
US05668152

Reaction notes

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