HCID 11133305, compound → HCID 11090513, compound

HRID 1826083Notes

Reaction equation

HRID 1826083 reaction equation
[CH2:1]([CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([C:16](=O)[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:9]=1)[C:4]([OH:6])=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([CH:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=2)[CH:9]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 11133305HCID 11133305, compound

Product 1

HCID 11090513HCID 11090513, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-ethyl-3-[3-[3-[4-(trifluoromethyl)phenyl]propionyl]-4-methoxyphenyl]propanoic acid (224 mg, 0.548 mmol) in ethanol (30 mL) was hydrogenated for 7 hours with 10% palladium on carbon (250 mg) at room temperature under a hydrogen pressure of 392 kPa. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by means of thin layer silica gel column chromatography (eluent: n-hexane: ethyl acetate:acetic acid=200:100:2 v/v/v) to afford 185 mg (86%) of the title compound as a yellow oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by means of thin layer silica gel column chromatography (eluent: n-hexane: ethyl acetate:acetic acid=200:100:2 v/v/v)

Sources & evidence

ORD record
ord-a691f93045f9401d856409afc2151d4f
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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