Methanol → HCID 178472972, Verbindung

HRID 2225591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225591
C(=O)([O-])[O-].[K+].[K+].CO.[CH3:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17](=[O:29])[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([O:27][CH3:28])[CH:21]=2)[CH2:12][CH2:11]1.Br[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]>CC(CC(C)C)=O>[CH3:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([NH:16][C:17](=[O:29])[CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:22]([O:27][CH3:28])[CH:21]=2)[CH2:14][CH2:15]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178490515HCID 178490515, Verbindung

Produkt 1

HCID 178472972HCID 178472972, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

20.7 g of potassium carbonate and 5 ml of methanol were added to a solution of 28.9 g of N-(trans-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (Example 131) in 600 ml of methylisobutylketone. The solution was reacted for 30 minutes, while it was refluxed. Next, 27.7 ml of ethyl bromoacetate was added dropwise into the solution over about 20 minutes by means of a dropping funnel. Thereafter, the solution was stirred for 4 hours. After reaction, the solution was allowed to cool to room temperature. After the potassium carbonate has been filtered out from the filtrate, the solvent was removed in vacuo from the filtrate. The product obtained was recrystallized from methylene chloride/ether, yielding 35.2 g of N-(trans-4-methylcyclohexyl)-4-(ethoxycarbonylmethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Aufarbeitung

  1. customThe solution was reacted for 30 minutes, while it
  2. temperaturewas refluxed
  3. customAfter reaction
  4. filtrationAfter the potassium carbonate has been filtered out from the filtrate
  5. customthe solvent was removed in vacuo from the filtrate
  6. customThe product obtained
  7. customwas recrystallized from methylene chloride/ether

Quellen und Nachweise

ORD-Eintrag
ord-79aec66bc9424caaa44825dbd38fa071
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344845

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