4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid benzyl ester → 4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid

HRID 1425Notes

Reaction equation

HRID 1425 reaction equation
C([O:8][C:9](=[O:30])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][C@@H:19]([C:26]([F:29])([F:28])[F:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:17])=[CH:12][CH:11]=1)C1C=CC=CC=1.[H][H]>[Pd].O1CCCC1>[F:27][C:26]([F:28])([F:29])[C@H:19]([O:18][C:16]([C:13]1[CH:14]=[CH:15][C:10]([C:9]([OH:30])=[O:8])=[CH:11][CH:12]=1)=[O:17])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 545493634-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 544396714-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acidYield 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Then, 0.07 g of 5% palladium/carbon and 10 ml of a tetrahydrofuran solution containing 0.63 g of 4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid benzyl ester were stirred overnight at room temperature in a stream of hydrogen to decompose a benzyl protective group by hydrogenation. 5% palladium/carbon was removed using Celite as a filter aid, and the filtrate was concentrated. The concentrate obtained was purified by column chromatography to obtain 0.49 g of 4-((R)-1-trifluoromethylheptyloxycarbonyl)benzoic acid as a colorless liquid (gradually crystallized) (isolated yield: 98%).

Workup

  1. custom5% palladium/carbon was removed
  2. concentrationthe filtrate was concentrated
  3. customThe concentrate obtained
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-679c764250d94da2b08939ad59ce9559
Source dataset
uspto-grants-1998_03
Patent number
US05725798

Reaction notes

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