Sodium Hydroxide → HCID 15057649, compound

HRID 654033Notes

Reaction equation

HRID 654033 reaction equation
C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([C:12](=[O:19])[NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:6]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)C.[OH-].[Na+]>O1CCOCC1>[CH2:21]([O:20][C:6]1[C:7]([C:12](=[O:19])[NH:13][CH2:14][C:15]([F:16])([F:17])[F:18])=[CH:8][C:9]([F:11])=[CH:10][C:5]=1[C:4]([OH:28])=[O:3])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 150576482-Benzyloxy-5-fluoro-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid ethyl ester

Product 1

HCID 15057649HCID 15057649, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

10.78 g (27 mmol) of 2-benzyloxy-5-fluoro-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid ethyl ester is dissolved in 60 ml of dioxane, the solution is mixed with 17.5 ml (35 mmol) of 2N sodium hydroxide solution, stirred for 1 hour at room temperature and 1 hour at 40° C. The reaction mixture is concentrated by evaporation under reduced pressure, the residue is taken up in 80 ml of water, acidified to pH 1 with concentrated hydrochloric acid. In this case, the acid precipitates mostly at amorphous solid. It is suctioned off and washed with a little water. The aqueous phase is shaken out several times with ethyl acetate. The ethyl acetate extract is concentrated by evaporation and the residue is combined with the precipitate from the water. It is dried in a vacuum for 48 hours at 50° C. Yield: 8.38 g (22.57 mmol) =83.6% of the theoretical yield is obtained as an amorphous solid.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation under reduced pressure
  2. customIn this case, the acid precipitates mostly at amorphous solid
  3. washwashed with a little water
  4. stirringThe aqueous phase is shaken out several times with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. concentrationis concentrated by evaporation
  7. customIt is dried in a vacuum for 48 hours at 50° C
  8. customYield: 8.38 g (22.57 mmol) =83.6% of the theoretical yield
  9. customis obtained as an amorphous solid

Sources & evidence

ORD record
ord-ea1174608aeb4bfea10cc91f12ca8abe
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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