Sodium Azide → HCID 86678296, compound

HRID 2205012Notes

Reaction equation

HRID 2205012 reaction equation
[F:1][C:2]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([F:7])[CH2:3][CH2:4][CH2:5]I.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:16]([CH2:5][CH2:4][CH2:3][C:2]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([F:7])[F:1])=[N+:17]=[N-:18]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14632758HCID 14632758, compound

Product 1

HCID 86678296HCID 86678296, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 1,1-difluoro-4-iodobutylphosphonate (1 eq) in DMF (0.27 M) was added sodium azide (3 eq). The reaction mixture was stirred at room temperature for 90 minutes. The mixture was diluted with ethyl acetate and washed with water. The aqueous phase was back extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 10-50% EtOAc/Hex to give the product as a yellowish oil.

Workup

  1. washwashed with water
  2. extractionThe aqueous phase was back extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated en vaccuo
  6. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-4659ae03953e40db98649cfdf2fb8bd1
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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