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HCID 58392355, Verbindung → HCID 58392206, Verbindung

HRID 561392
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561392
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH:9]2C(=O)O[C:12](C)([CH3:16])[O:11][C:10]2=[O:18])=[CH:4][CH:3]=1>N1C=CC=CC=1.C(O)C.[Cu]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[C:27]3[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:9][C:10]([O:11][CH2:12][CH3:16])=[O:18])=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

HCID 58392355HCID 58392355, Verbindung

Produkt 1

HCID 58392206HCID 58392206, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 702EthanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

18 mg (0.28 mmol) of copper powder were added to 12.2 g (27.5 mmol) of the compound from Example 13A in 200 ml of pyridine and 55 ml of ethanol. The reaction mixture was heated under reflux for 4 h. It was concentrated, and the residue was taken up in dichloromethane, washed with water, 1N hydrochloric acid and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient). 6.68 g (56% of theory) of the target compound were obtained.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationIt was concentrated
  4. washwashed with water, 1N hydrochloric acid and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)
  9. custom6.68 g (56% of theory) of the target compound were obtained

Quellen und Nachweise

ORD-Eintrag
ord-55d35807f9f24c6aaa3bd797bcc94395
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063234B2

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