Hydrochloric Acid → HCID 11133305, compound

HRID 1826082Notes

Reaction equation

HRID 1826082 reaction equation
C([O:3][C:4](=[O:36])[CH:5]([CH2:34][CH3:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([C:15](=[O:33])[CH:16](C(OCC)=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[CH:8]=1)C.Cl>C(O)(=O)C>[CH2:34]([CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([C:15](=[O:33])[CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:22][CH:23]=2)[CH:8]=1)[C:4]([OH:36])=[O:3])[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11049452HCID 11049452, compound

Product 1

HCID 11133305HCID 11133305, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl-3-[3-[2-ethoxycarbonyl-3-[4-(trifluoromethyl)phenyl]propionyl]-4-methoxyphenyl]-2-ethylpropanoate (2.62 g, 5.15 mmol), glacial acetic acid (10 mL) and concentrated hydrochloric acid (5 mL) was refluxed for 5 hours. After cooling, the mixture was poured into ice water, which was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate:acetic acid=400:100:1.5 v/v/v) to afford 1.47 g (70%) of the title compound as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate:acetic acid=400:100:1.5 v/v/v)

Sources & evidence

ORD record
ord-046e356edd5f4739915ae5510a6246b9
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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