Ammonium Acetate → HCID 69053468, compound

HRID 860624Notes

Reaction equation

HRID 860624 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7](=O)[CH:8]([O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH2:9][CH3:10])=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:29]>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][C:7]1[N:29]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[O:11][C:8]=1[CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 69056835HCID 69056835, compound

Product 1

HCID 69053468HCID 69053468, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Trifluoromethyl-benzoic acid 3-ethoxycarbonyl-1-ethyl-2-oxo-propyl ester (25 mmol) is dissolved in acetic acid (100 mL) and dry ammonium acetate (10 g, 100 mmol) is added, then the reaction is heated under nitrogen to reflux. The reaction is monitored by TLC and HPLC but complete consumption of the starting material is never observed, and then allowed to cool. The cooled reaction is concentrated and diluted with 250 mL ethyl acetate. The residue is washed with 100 mL saturated sodium bicarbonate followed by water and brine. The organic layer is dried over anhydrous sodium sulfate, then concentrated and purified by column chromatrography. The fractions that contained pure product are concentrated to yield [5-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-acetic acid ethyl ester (4.0 g, 12.22 mmol) or 50% yield.

Workup

  1. temperaturethe reaction is heated under nitrogen
  2. temperatureto reflux
  3. customThe reaction is monitored by TLC and HPLC but complete consumption of the starting material
  4. temperatureto cool
  5. customThe cooled reaction
  6. concentrationis concentrated
  7. additiondiluted with 250 mL ethyl acetate
  8. washThe residue is washed with 100 mL saturated sodium bicarbonate
  9. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. custompurified by column chromatrography
  12. concentrationare concentrated

Sources & evidence

ORD record
ord-13991a961bfa44f7bf994de3b7e772f5
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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