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

HRID 1269553
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1269553
C([O:3][C:4](=[O:38])[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([C:21]3[S:25][C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=4)=[N:23][C:22]=3[CH3:36])=[O:20])[CH2:14]2)[CH:10]=[CH:9][C:8]=1[CH3:37])C.C(=O)([O-])[O-].[K+].[K+].CO>O>[CH3:37][C:8]1[CH:9]=[CH:10][C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([C:21]3[S:25][C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:28][CH:27]=4)=[N:23][C:22]=3[CH3:36])=[O:20])[CH2:14]2)=[CH:12][C:7]=1[NH:6][CH2:5][C:4]([OH:38])=[O:3]
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Komponenten

5

Edukt 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 68884771(2-Methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl ester

Produkt 1

HCID 18448467(2-Methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acidAusbeute 110,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of (2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid ethyl ester (19 mg, 0.035 mmol), potassium carbonate (10 mg, 0.07 mmol), methanol (5 mL) and water (1 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 20 mg (99%) of (2-methyl-5-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbonyl]-piperidin-3-yl}-phenylamino)-acetic acid as a white solid.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-be26f5131be94b7dad58473ee67b5b0f
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07199243B2

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