2-Benzyloxy-5-fluoro-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid → 5-Fluoro-2-hydroxy-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid

HRID 654034Notes

Reaction equation

HRID 654034 reaction equation
C([O:8][C:9]1[C:17]([C:18](=[O:25])[NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]([F:26])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:26][C:15]1[CH:16]=[C:17]([C:18](=[O:25])[NH:19][CH2:20][C:21]([F:23])([F:24])[F:22])[C:9]([OH:8])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 150576492-Benzyloxy-5-fluoro-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid

Product 1

HCID 150576505-Fluoro-2-hydroxy-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5.2 g (14 mmol) of 2-benzyloxy-5-fluoro-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid is dissolved in 30 ml of ethanol. 250 mg of palladium-carbon (10%) is added and is hydrogenated in 1 hour at normal temperature. The catalyst is then filtered off and the filtrate is evaporated to dryness in a vacuum. The residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol. 3.03 g (11.34 mmol)=81% of the theoretical yield of the compound is obtained as an amorphous solid.

Workup

  1. filtrationThe catalyst is then filtered off
  2. customthe filtrate is evaporated to dryness in a vacuum
  3. customThe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol
  4. custom3.03 g (11.34 mmol)=81% of the theoretical yield of the compound is obtained as an amorphous solid

Sources & evidence

ORD record
ord-03e5e5dcaa544798b60c2dc67ed7b4b7
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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