Sodium Azide → HCID 10037399, compound

HRID 1822469Notes

Reaction equation

HRID 1822469 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][N:20]=[N+:21]=[N-:22])[CH2:16][CH:17]([CH3:19])[CH3:18])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10379776HCID 10379776, compound

Product 1

HCID 10037399HCID 10037399, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mesylate from step i (32.6 g, 110 mmol) was treated with sodium azide (21.45 g, 330 mmol) in DMF at 80° C. for 24 hrs. The solvent was evaporated, the residue was taken up in DCM, filtered and washed with saturated NaHCO3 (aq). The solution was dried with Na2SO4 and concentrated to a brown oil which was purified by flash chromatography using a gradient of ethyl acetate and hexane to afford the title compound as a white solid (19.55 g, 73%).

Workup

  1. customThe solvent was evaporated
  2. filtrationfiltered
  3. washwashed with saturated NaHCO3 (aq)
  4. dry with materialThe solution was dried with Na2SO4
  5. concentrationconcentrated to a brown oil which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-8241f01eb32a4f4d9ce07aeddecec178
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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