Sodium Azide → HCID 58288500, compound

HRID 1969048Notes

Reaction equation

HRID 1969048 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23]OS(C)(=O)=O)[CH:7]=1)[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:30]=[N+:31]=[N-:32])[CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58288540HCID 58288540, compound

Product 1

HCID 58288500HCID 58288500, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

[3-(2-Methanesulfonyloxymethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid ethyl ester (1.0 mmol) and sodium azide (0.195 g, 3.0 mmol) were combined in DMF (10 mL) and stirred at 80° C. for 1 hour. Once no starting material was seen by analytical LCMS, the mixture was cooled to room temperature and partitioned between EtOAc and H2O. The aqueous layer was separated and extracted twice with EtOAc, and the combined organic layers were washed three times with H2O, and then dried and concentrated. The residue was purified by silica gel chromatography (0-10% EtOAc in hexanes) to give the title compound.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. custompartitioned between EtOAc and H2O
  3. customThe aqueous layer was separated
  4. extractionextracted twice with EtOAc
  5. washthe combined organic layers were washed three times with H2O
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d96f44907a164cca8c4362e13830e6b9
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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