Ethyl bromoacetate → HCID 13338732, Verbindung

HRID 485670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 485670
[N:1]([CH:4]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[NH:6][C:5]1=[O:17])=[N+:2]=[N-:3].CC(C)([O-])C.[K+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[N:1]([CH:4]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[N:6]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:5]1=[O:17])=[N+:2]=[N-:3]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 13338731HCID 13338731, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 13338732HCID 13338732, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 3-azido-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one (8.9 g) in dry dimethylformamide (100 ml) is added during 30 minutes to a solution of potassium t-butoxide (4.5 g) in dry dimethylformamide (100 ml) maintained at 0° under an atmosphere of dry nitrogen. The reaction mixture is stirred at 0° for 2 hours, when a solution of ethyl bromoacetate (5.8 g) in dimethylformamide (10 ml) is added during 5 minutes. The reaction mixture is stirred at 0° for 2 hours, then evaporated under reduced pressure. The residue is distributed between ethyl acetate (250 ml) and water (150 ml), and the ethyl acetate solution washed with water (100 ml) and dried over sodium sulfate. The solvent is removed under reduced pressure to give 3-azido-1-ethoxycarbonylmethyl-1,3,4,5,6,7-hexahydro-1-benzazonin-2-one.

Aufarbeitung

  1. temperaturemaintained at 0° under an atmosphere of dry nitrogen
  2. stirringThe reaction mixture is stirred at 0° for 2 hours
  3. customevaporated under reduced pressure
  4. washthe ethyl acetate solution washed with water (100 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-da8be1d2d8214dbd9b0ed27eb1c3bc49
Quelldatensatz
uspto-grants-1985_08
Patentnummer
US04537885

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