2-Dimethylamino-2-(p-isobutylphenyl)propionic acid-2,2,2-trifluoroethyl ester → Ibuprofen trifluoroethyl ester

HRID 26454Notes

Reaction equation

HRID 26454 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][O:4][C:5](=[O:21])[C:6](N(C)C)([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=1)[CH3:7]>CO.[C].[Pd]>[F:1][C:2]([F:22])([F:23])[CH2:3][O:4][C:5](=[O:21])[CH:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:16])[CH3:17])=[CH:10][CH:9]=1)[CH3:7]

Participants

4

Reactant 1

HCID 213233072-Dimethylamino-2-(p-isobutylphenyl)propionic acid-2,2,2-trifluoroethyl ester

Product 1

HCID 21323312Ibuprofen trifluoroethyl esterYield 79%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 0.80 g of 2-dimethylamino-2-(p-isobutylphenyl)propionic acid-2,2,2-trifluoroethyl ester in 20 ml of methanol was added 0.22 g of palladium-carbon(10%). Hydrogenation was carried out at 50°-60° C. for 5 hours. After the reaction was complete, the catalyst was removed by filtration and the filtrate produced was freed of solvent by distillation to give an oily product. This product was distilled in vacuo to give 0.55 g of 2-(p-isobutylphenyl)propionic acid-2,2,2-trifluoroethyl ester as a colorless oil. Mass spectrum: parent ion 288 m/e.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe filtrate produced
  3. distillationwas freed of solvent by distillation
  4. customto give an oily product
  5. distillationThis product was distilled in vacuo

Sources & evidence

ORD record
ord-4ff5209fcb2f45bc8cb7d36f521148fd
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Reaction notes

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