Sodium Azide → HCID 14548440, compound

HRID 1987591Notes

Reaction equation

HRID 1987591 reaction equation
[N-:1]=[N+]=[N-].[Na+].Br[CH:6]([CH:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>CN(C=O)C.CCOC(C)=O>[CH2:10]([O:9][C:7](=[O:8])[CH:6]([NH2:1])[CH:12]([CH3:17])[C:13]([F:16])([F:15])[F:14])[CH3:11]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 3701096ETHYL 2-BROMO-3-METHYL-4,4,4-TRIFLUOROBUTYRATE

Product 1

HCID 14548440HCID 14548440, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (1.9 g, 28.7 mmol) and ethyl 2-bromo-3-methyl-4,4,4-trifluorobutyrate (5 g, 19.2 mmol) were placed in DMF (20 mL) and stirred for 48 h. The mixture was diluted with EtOAc (200 mL) and washed with brine (4×100 mL). The organic layer was dried over Na2SO4 and solvent was removed. The crude oil was placed in EtOH (20 mL) with 5% Pd/C (1.6 g) and shaken for 6 hours under H2 (50 psi). The reaction was filtered through the Celite® reagent and solvent was removed providing a clear oil (1.9 g) in 50% yield.

Workup

  1. washwashed with brine (4×100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4 and solvent
  3. customwas removed
  4. stirringshaken for 6 hours under H2 (50 psi)
  5. filtrationThe reaction was filtered through the Celite® reagent and solvent
  6. customwas removed

Sources & evidence

ORD record
ord-5d46f0754e3b48a9983060335b866e62
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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