Diethyl benzamidomalonate → Ethyl 2-(7-benzoylamino-7,7-bis(ethoxycarbonyl)-heptyloxy)-2-methylpropionate

HRID 1796359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796359
[O-][CH2:2]C.[Na+].C(O)C.[C:8]([NH:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]([CH3:42])([CH3:41])[C:37]([O:39][CH3:40])=[O:38]>C(O)C>[C:8]([NH:16][C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]([CH3:42])([CH3:41])[C:37]([O:39][CH2:40][CH3:2])=[O:38])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 3

HCID 66790Diethyl benzamidomalonateHCID 21866674Methyl 6-bromohexyloxy-2-methylpropionateHCID 23706232Ethanol sodium ethoxide

Produkt 1

HCID 21866624Ethyl 2-(7-benzoylamino-7,7-bis(ethoxycarbonyl)-heptyloxy)-2-methylpropionateAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To 5 ml of dry ethanol, 675 mg of 20% sodium ethoxide-ethanol solution and 698 mg of diethyl benzoylaminomalonate were added, and stirred for 30 minutes at room temperature. Then, a solution of 914 mg of methyl 6-bromohexyloxy-2-methylpropionate/4 ml of dry ethanol was added dropwise, and stirred for 15 hours at 50–60° C. The reaction solution was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=5:1) to provide 642 mg of the objective compound as yellowish oil.

Aufarbeitung

  1. stirringstirred for 15 hours at 50–60° C
  2. additionThe reaction solution was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-4b7455017fed48efbf1bd318a8cb20f2
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030143B2

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