HCID 68960562, compound → HCID 57667902, compound

HRID 2191664Notes

Reaction equation

HRID 2191664 reaction equation
[CH:1]1([C:6]2[CH:18]=[CH:17][C:9]([C:10]([O:12]C(C)(C)C)=[O:11])=[C:8]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:7]=2)[CH2:5][CH2:4][CH:3]=[CH:2]1>[C].[Pd].CO>[CH:1]1([C:6]2[CH:18]=[CH:17][C:9]([C:10]([OH:12])=[O:11])=[C:8]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 68960562HCID 68960562, compound

Product 1

HCID 57667902HCID 57667902, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To methanol 2.0 mL solution of tert-butyl 4-(2-cyclopenten-1-yl)-2-(4-fluoroanilino)benzoate 45 mg was added 5% palladium-carbon 9 mg, and it was stirred under hydrogen atmosphere at room temperature for 6 hours. Insoluble matter was filtrated, and the solvent was removed under reduced pressure. Trifluoroacetic acid 10 mL was added to the obtained residue, and it was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure, methanol was added to the obtained residue, and solid matter was filtrated to give 4-cyclopentyl-2-(4-fluoroanilino)benzoic acid 24 mg of white solid.

Workup

  1. filtrationInsoluble matter was filtrated
  2. customthe solvent was removed under reduced pressure
  3. additionTrifluoroacetic acid 10 mL was added to the obtained residue, and it
  4. stirringwas stirred at room temperature for 1 hour
  5. customThe solvent was removed under reduced pressure, methanol
  6. additionwas added to the obtained residue, and solid matter
  7. filtrationwas filtrated

Sources & evidence

ORD record
ord-4bea88f9b49c4ead8c1b77ff04ca5f4e
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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