1-Bromo-4-chlorobutane → Ethyl 6-chloro-2-ethoxycarbonyl-2-(p-toluoylamino)hexanoate

HRID 857233

Reaktionsgleichung

Reaktionsgleichung von HRID 857233
[Na].[C:2]1([CH3:22])[CH:7]=[CH:6][C:5]([C:8]([NH:10][CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][Cl:28]>C(O)C>[Cl:28][CH2:27][CH2:26][CH2:25][CH2:24][C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([NH:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:22])=[CH:3][CH:4]=1)=[O:9])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 813641-Bromo-4-chlorobutaneHCID 5360545SodiumHCID 17447783Diethyl p-toluoylaminomalonate

Produkt 1

HCID 21866781Ethyl 6-chloro-2-ethoxycarbonyl-2-(p-toluoylamino)hexanoateAusbeute 54,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium (6.42 g) was dissolved in 390 ml of ethanol at room temperature. To the solution was added 78.0 g of diethyl p-toluoylaminomalonate, and 47.9 g of 1-bromo-4-chlorobutane was added dropwise under heating to reflux. The mixture was heated to reflux for 20 hours. The reaction solution was concentrated. To the residue was added water, and the mixture was washed with ethyl acetate. After washing with 10% hydrochloric acid and water sequentially, the solution was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=9:1) to provide 55.7 g of the objective compound as colorless oil.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureunder heating to reflux
  3. temperatureThe mixture was heated
  4. temperatureto reflux for 20 hours
  5. concentrationThe reaction solution was concentrated
  6. additionTo the residue was added water
  7. washthe mixture was washed with ethyl acetate
  8. washAfter washing with 10% hydrochloric acid and water sequentially
  9. dry with materialthe solution was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d6e607109e0a497a9a79d0630c045c72
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144906B2

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