Hydrochloric Acid → Ethyl Acetate

HRID 854590Notes

Reaction equation

HRID 854590 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:23][CH:22]=3)[S:18][C:19]=2[CH3:20])=[CH:8][C:7]=1[CH3:33].[OH-:35].[Na+].Cl>O1CCCC1.C(OCC)(=O)C>[CH3:33][C:7]1[CH:8]=[C:9]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:23][CH:22]=3)[S:18][C:19]=2[CH3:20])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:34])=[O:2].[C:9]([O:12][CH2:13][CH3:14])(=[O:35])[CH3:8]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69141239HCID 69141239, compound

Product 2

HCID 8857Ethyl AcetateYield 87%HCID 10195274HCID 10195274, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Methyl-4-{2-[5-methyl-2-(4-pyridin-3-yl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-propionic acid methyl ester (47 mg, 0.100 mmol) is dissolved in tetrahydrofuran (1 mL) and 5N sodium hydroxide (1 mL) solution is added at room temperature. The reaction is heated to reflux and monitored by HPLC. Upon complete conversion, the reaction is allowed to cool to room temperature and neutralized with 5N hydrochloric acid (1 mL), diluted with ethyl acetate, and extracted. The organic layer is washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The pure 3-(2-Methyl-4-{2-[5-methyl-2-(4-pyridin-3-yl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-propionic acid (40 mg, 0.087 mmol) may also be obtained by recrystalization from ethyl acetate (87% yield). MS (ES): 459.2 (M++1). Alternatively, the acid may be obtained after reversed phase preparative HPLC as the hydrochloride salt.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux
  3. extractionextracted
  4. washThe organic layer is washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3098831b7c3f438499c2f3845f27e390
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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