HCID 19888147, compound → HCID 19888143, compound

HRID 654045Notes

Reaction equation

HRID 654045 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][NH:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([NH:13][C:14](=[O:20])[CH2:15][O:16]C(=O)C)[C:7]=1[OH:21]>[OH-].[Na+]>[F:24][C:2]([F:1])([F:23])[CH2:3][NH:4][C:5](=[O:22])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([NH:13][C:14](=[O:20])[CH2:15][OH:16])[C:7]=1[OH:21]

Participants

3

Reactant 1

HCID 19888147HCID 19888147, compound

Product 1

HCID 19888143HCID 19888143, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
40 °C

Procedure

5.9 g (17 mmol) of 3-acetoxyacetamido-5-fluoro-2-hydroxy-benzoic acid-(2,2,2,-trifluoro-ethyl)amide is dissolved in 34 ml of 1N NaOH and stirred for 30 minutes at 40° C. The reaction solution is then cooled to room temperature and filtered over 200 ml of cation exchanger. The eluate is evaporated to dryness in a vacuum and the residue is chromatographed on silica gel 60 with ethyl acetate/acetone. 3.3 g=62.7% of the theoretical yield is obtained as an amorphous material.

Workup

  1. temperatureThe reaction solution is then cooled to room temperature
  2. filtrationfiltered over 200 ml of cation exchanger
  3. customThe eluate is evaporated to dryness in a vacuum
  4. customthe residue is chromatographed on silica gel 60 with ethyl acetate/acetone
  5. custom3.3 g=62.7% of the theoretical yield
  6. customis obtained as an amorphous material

Sources & evidence

ORD record
ord-fb9351f1250a4cdf88d59f8520f5a317
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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