Potassium Carbonate → 4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid

HRID 925278Notes

Reaction equation

HRID 925278 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([CH3:11])=[N:8][C:7]=1[S:12][CH2:13][CH2:14][C:15]([F:24])([F:23])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:5])C.C(=O)([O-])[O-].[K+].[K+]>CCO>[F:24][C:15]([F:23])([C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH2:14][CH2:13][S:12][C:7]1[N:8]=[C:9]([CH3:11])[S:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 867201714-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 867201724-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid ethyl ester (0.6 g, 1.6 mmol) in EtOH (1.5 ml) is added an aqueous solution (1.5 ml) of potassium carbonate (0.22 g, 4.0 mmol) and the mixture is stirred at RT for 16 h. After completion of the reaction, the solvent is evaporated and the residue is diluted with water (30 ml), acidified with 2M hydrochloric acid to pH 3 and extracted with EtOAc (3×40 ml) yielding 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-2-methyl-thiazole-5-carboxylic acid (0.41 g, 1.19 mmol, 74%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent is evaporated
  3. additionthe residue is diluted with water (30 ml)
  4. extractionextracted with EtOAc (3×40 ml)

Sources & evidence

ORD record
ord-d5f1ff0f41fb4104af8db1a0a2c6cfab
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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