Hydrochloric Acid → Ethyl Acetate

HRID 860697Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860697
C[O:2][C:3](=[O:35])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:24][CH:23]=3)[S:19][C:20]=2[CH3:21])[CH3:15])=[CH:8][C:7]=1[CH3:34].[OH-:36].[Na+].Cl>O1CCCC1.C(OCC)(=O)C>[CH3:34][C:7]1[CH:8]=[C:9]([O:12][CH2:13][CH:14]([C:16]2[N:17]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:24][CH:23]=3)[S:19][C:20]=2[CH3:21])[CH3:15])[CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][C:3]([OH:35])=[O:2].[C:9]([O:12][CH2:13][CH3:14])(=[O:36])[CH3:8]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58765697HCID 58765697, Verbindung

Produkt 2

HCID 8857Ethyl AcetateAusbeute 68 %HCID 10310884HCID 10310884, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-(2-Methyl-4-{2-[5-methyl-2-(4-pyrimidin-2-yl-phenyl)-thiazol-4-yl]-propoxy}-phenyl)-propionic acid methyl ester (698 mg, 1.43 mmol) is dissolved in tetrahydrofuran (2 mL) and 5N sodium hydroxide (2 mL) solution is added with stirring 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 (2 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-pyrimidin-2-yl-phenyl)-thiazol-4-yl]-propoxy}-phenyl)-propionic acid (462 mg, 0.9755 mmol) may also be obtained by recrystalization from ethyl acetate (68% yield), MS (ES): ?? (M++1).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-197862121bdf4fb782c4b923840925c9
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153878B2

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