Sodium Azide → HCID 11099148, compound

HRID 1357503Notes

Reaction equation

HRID 1357503 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:13][C@H:14]1[C@@H:19]2[O:20]S(=O)O[C@@H:18]2[CH:17]=[C:16]([C:24]([O:26][CH3:27])=[O:25])[CH2:15]1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C=O)C.CCOC(C)=O>[C:5]([O:13][C@H:14]1[C@H:19]([OH:20])[C@@H:18]([N:1]=[N+:2]=[N-:3])[CH:17]=[C:16]([C:24]([O:26][CH3:27])=[O:25])[CH2:15]1)(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 71534413HCID 71534413, compound

Product 1

HCID 11099148HCID 11099148, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (2.3 g, 36.0 mmol) was added to a solution of Example 13F in DMF (30 mL). After stirring at room temperature overnight, the reaction mixture was diluted with EtOAc, washed with brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography using hexanes/ethyl acetate (3/2) to afford 1.36 g (36%) of the desired product as a colorless oil.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography

Sources & evidence

ORD record
ord-d2dbfa2bbc4c4a739ba6651dfdf1c9ee
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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