Sodium Azide → HCID 91005463, compound

HRID 1434883Notes

Reaction equation

HRID 1434883 reaction equation
S(O[CH2:6][C@@:7]12[CH2:22][O:21][C@@H:9]([C@H:10]([N:12]3[CH:19]=[C:18]([CH3:20])[C:16](=[O:17])[NH:15][C:13]3=[O:14])[O:11]1)[C@@H:8]2[OH:23])(C)(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([CH2:6][C@@:7]12[CH2:22][O:21][C@@H:9]([C@H:10]([N:12]3[CH:19]=[C:18]([CH3:20])[C:16](=[O:17])[NH:15][C:13]3=[O:14])[O:11]1)[C@@H:8]2[OH:23])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 87357620HCID 87357620, compound

Product 1

HCID 91005463HCID 91005463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dimethylformamide (3.0 ml) solution of Compound 3 (27 mg, 0.078 mmol) and sodium azide was stirred for 1.5 hours at room temperature and for 2 hours at 100° C. in a stream of nitrogen. The solvent was distilled off under reduced pressure, and then a small amount of water was added to the residue, followed by extracting the mixture with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain Compound 4 (28 mg, quant. in 2 steps) as a yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additiona small amount of water was added to the residue
  3. extractionby extracting the mixture with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f61ee213a3294ac488e7f9a15487e7d9
Source dataset
uspto-grants-2009_11
Patent number
US07615619B2

Reaction notes

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