Benzyl 2'-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylate → 2'-(3-Tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylic acid

HRID 1026559Notes

Reaction equation

HRID 1026559 reaction equation
[C:1]([O:5][C:6](=[O:35])[C:7]([CH3:34])([CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])=[C:18]([F:32])[CH:17]=1)([CH3:4])([CH3:3])[CH3:2]>O.O1CCCC1.[C].[Pd]>[C:1]([O:5][C:6](=[O:35])[C:7]([CH3:34])([CH3:33])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([OH:24])=[O:23])=[C:18]([F:32])[CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 68006312Benzyl 2'-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylate

Product 1

HCID 680062602'-(3-Tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylic acidYield 68.8%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solvent solution of benzyl 2′-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylate (15.0 g) in water (75 ml) and tetrahydrofuran (300 ml) was added 10% palladium carbon (4.50 g), followed by stirring at room temperature for 7 hours under a hydrogen atmosphere. The reaction solution was filtered through Celite, and washed with methanol, and then the filtrate was concentrated under reduced pressure. The residue was dissolved in dichloromethane, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford 2′-(3-tert-butoxy-2,2-dimethyl-3-oxopropoxy)-3-fluorobiphenyl-4-carboxylic acid (8.38 g).

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d0a02c745034adabb597dd5ddbd160a
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

Loading…