Methanol → 2-Methyl-2-(2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenoxy)-propionic acid

HRID 1269534Notes

Reaction equation

HRID 1269534 reaction equation
C([O:3][C:4](=[O:40])[C:5]([CH3:39])([O:7][C:8]1[CH:13]=[C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([C:22]3[S:26][C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=4)=[N:24][C:23]=3[CH3:37])=[O:21])[CH2:15]2)[CH:11]=[CH:10][C:9]=1[CH3:38])[CH3:6])C.C(=O)([O-])[O-].[K+].[K+].CO>O>[CH3:39][C:5]([O:7][C:8]1[CH:13]=[C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:20]([C:22]3[S:26][C:25]([C:27]4[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][CH:28]=4)=[N:24][C:23]=3[CH3:37])=[O:21])[CH2:15]2)[CH:11]=[CH:10][C:9]=1[CH3:38])([CH3:6])[C:4]([OH:40])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 688866962-Methyl-2-(2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenoxy)-propionic acid ethyl ester

Product 1

HCID 102568882-Methyl-2-(2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenoxy)-propionic acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methyl-2-(2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenoxy)-propionic acid ethyl ester (179 mg, 0.31 mmol), potassium carbonate (86 mg, 0.62 mmol), methanol (10 mL) and water (2 mL) was heated at reflux for 3 h, cooled to room temperature and concentrated under reduced pressure. The resulting residue was taken up in water (50 mL), acidified with 1N aqueous hydrochloric acid and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to yield 151 mg (89%) of 2-methyl-2-(2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenoxy)-propionic acid as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7040ce65016742f98929ecbe50dc2633
Source dataset
uspto-grants-2007_04
Patent number
US07199243B2

Reaction notes

Loading…