Potassium Hydroxide → HCID 19785561, compound

HRID 256772Notes

Reaction equation

HRID 256772 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:20][CH3:21])[S:13][C:14]=2[C:15]([O:17]CC)=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.[OH-].[K+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([C:10]2[N:11]=[C:12]([NH:20][CH3:21])[S:13][C:14]=2[C:15]([OH:17])=[O:16])[CH3:9])[CH:5]=[CH:4][C:3]=1[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 9822392HCID 9822392, compound

Product 1

HCID 19785561HCID 19785561, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Ethyl 4-(1-(2,4'-difluoro-4-biphenylyl)ethyl)-2-methylamino-5-thiazolecarboxylate (1.00 g, 2.48 mmole) was dissolved in methanol (20 ml). After adding a solution of potassium hydroxide (420 mg, 7.49 mmole) in water (4 ml), the mixture was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and washed with ether. The water layer was acidified to about pH 4 with 1chloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure Recrystallization of the residue from methanol gave the desired 4-(1-(2,4'-difluoro-4-biphenylyl-)ethyl)-2-methylamino-5-thiazolecarboxylic acid (599 mg, 1.60 mmoles, yield 65%) as a white crystalline product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionthe residue was diluted with water
  5. washwashed with ether
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. customdried
  9. concentrationconcentrated under reduced pressure Recrystallization of the residue from methanol

Sources & evidence

ORD record
ord-88e1a32042f248dea5b7f4ae719746dc
Source dataset
uspto-grants-1993_11
Patent number
US05258396

Reaction notes

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