Sodium Acetate → HCID 178470000, Verbindung

HRID 12895

Reaktionsgleichung

Reaktionsgleichung von HRID 12895
Cl.[NH:2]([CH:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)[NH2:3].[CH2:11]([O:13][C:14](=[O:26])[C:15](=[CH:22][N:23](C)C)[C:16](=O)[C:17]([F:20])([F:19])[F:18])[CH3:12].C([O-])(=O)C.[Na+]>C(O)C>[CH2:11]([O:13][C:14]([C:15]1[CH:22]=[N:3][N:2]([C@H:4]2[CH2:9][CH2:8][C@@H:7]([OH:10])[CH2:6][CH2:5]2)[C:16]=1[C:17]([F:18])([F:19])[F:20])=[O:26])[CH3:12].[CH2:11]([O:13][C:14]([C:15]1[CH:22]=[N:23][N:2]([C@H:4]2[CH2:9][CH2:8][C@H:7]([OH:10])[CH2:6][CH2:5]2)[C:16]=1[C:17]([F:20])([F:19])[F:18])=[O:26])[CH3:12]

Komponenten

6

Edukt 3

HCID 517045Sodium AcetateHCID 53979199Butanoic acid, 2-[(dimethylamino)methylene]-4,4,4-trifluoro-3-oxo-, ethyl esterHCID 67020985HCID 67020985, Verbindung

Produkt 2

HCID 178470000HCID 178470000, VerbindungAusbeute 27 %HCID 178470001HCID 178470001, VerbindungAusbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

4-Hydrazino-cyclohexanol, hydrochloride (0.255 g, 1.53 mmol, prepared in Example 67, Step 2), 2-dimethylaminomethylene-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester (0.272 g, 1.14 mmol) and anhydrous sodium acetate (0.256 g, 3.12 mmol) were combined in ethanol (2.0 mL) and heated at 70° C. under argon for 14 hours. After cooling to room temperature, the reaction mixture was partitioned between methylene chloride and water. The aqueous phase was washed a second time with methylene chloride. The two organic phases were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography (eluting with a 40-100% ethyl acetate-hexanes gradient) successfully separated the cis-trans isomers, yielding cis-1-(4-hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (96.1 mg, 27%) and trans-1-(4-hydroxy-cyclohexyl)-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (63.5 mg, 18%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between methylene chloride and water
  3. washThe aqueous phase was washed a second time with methylene chloride
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (
  8. washeluting with a 40-100% ethyl acetate-hexanes gradient)
  9. customsuccessfully separated the cis-trans isomers

Quellen und Nachweise

ORD-Eintrag
ord-659f1e75bc804add9ba602c4288f510a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728029B2

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