Sodium Azide → HCID 54119759, compound

HRID 355513Notes

Reaction equation

HRID 355513 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:19]([NH2:20])=[C:18]([C:21](=[O:24])[CH2:22]Cl)[N:17]=[CH:16]2)[C@@H:6]1[Cl:25])(=[O:3])[CH3:2].[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[C:19]([NH2:20])=[C:18]([C:21](=[O:24])[CH2:22][N:26]=[N+:27]=[N-:28])[N:17]=[CH:16]2)[C@@H:6]1[Cl:25])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 53739986HCID 53739986, compound

Product 1

HCID 54119759HCID 54119759, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound (39) obtained in step (5) above (170 mg) was dissolved in N,N-dimethylformamide (3.4 ml), to which was added sodium azide (45 mg). The resultant mixture was stirred at room temperature for 1 hour to conduct the reaction intended. The reaction solution obtained was concentrated and the residue was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated to leave a yellow syrup. The syrup was purified by silica gel column chromatography (developer solvent: toluene-ethyl acetate, 1:2) to afford the titled compound (40) as a colorless solid (159 mg). Yield: 92%.

Workup

  1. customThe reaction solution obtained
  2. concentrationwas concentrated
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto leave a yellow syrup
  8. customThe syrup was purified by silica gel column chromatography (developer solvent: toluene-ethyl acetate, 1:2)

Sources & evidence

ORD record
ord-943b7b085c884fc6969d708c4ddafda7
Source dataset
uspto-grants-1998_11
Patent number
US05831072

Reaction notes

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