Sodium Azide → HCID 58670155, compound

HRID 1353169Notes

Reaction equation

HRID 1353169 reaction equation
Br[CH2:2][C@H:3]1[O:7][C:6](=[O:8])[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C>[N:17]([CH2:2][C@H:3]1[O:7][C:6](=[O:8])[C@@H:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1)=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11781359HCID 11781359, compound

Product 1

HCID 58670155HCID 58670155, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred slurry of compound 1A, (8.47 g, 28.8 mmol) in 127 mL of DMF at room temperature was added sodium azide (2.25 g, 34.6 mmol). The reaction mixture was then heated to 60° C. under argon for 9 h. The reaction mixture was then cooled, quenched with 200 mL of ice-cold water and extracted four times with 200 mL portions of ether. The combined organic extracts were washed three times with water, once with saturated NaCl and dried over Na2SO4, then MgSO4, filtered and evaporated under reduced pressure. Purification by silica gel chromatography (3:17 EtOAc/CH2Cl2) provided the title compound (7.25 g, 98%) as a colorless oil. MS [M+Na]+: found 278.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customquenched with 200 mL of ice-cold water
  3. extractionextracted four times with 200 mL portions of ether
  4. washThe combined organic extracts were washed three times with water
  5. dry with materialonce with saturated NaCl and dried over Na2SO4
  6. filtrationMgSO4, filtered
  7. customevaporated under reduced pressure
  8. customPurification by silica gel chromatography (3:17 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-25ddc13ee3c74628a30b342184191cbe
Source dataset
uspto-grants-2007_05
Patent number
US07220859B2

Reaction notes

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