Water → Ethyl 2-(4-carbamoyl-1-imidazolyl)valerate

HRID 278464

Reaktionsgleichung

Reaktionsgleichung von HRID 278464
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]([NH2:10])=[O:9])[N:5]=[CH:4]1.Br[CH:12]([CH2:18][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14].O>CN(C=O)C>[C:8]([C:6]1[N:5]=[CH:4][N:3]([CH:12]([CH2:18][CH2:19][CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=1)(=[O:9])[NH2:10]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79071Ethyl 2-bromovalerateHCID 152917Imidazole-4-carboxamide

Produkt 1

HCID 22628554Ethyl 2-(4-carbamoyl-1-imidazolyl)valerate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

NaH (60% in mineral oil, 60 mg) was added to a stirred solution of 4-imidazolecarboxamide (obtained in Preparation 1) (167 mg) in DMF (3.5 ml), and the reaction mixture was stirred for 1.5 hours at 55° C. Ethyl 2-bromovalerate (0.153 ml) was added to this mixture, and the reaction mixture was stirred for 3 hours at 55-60° C. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel (12 g) chromatography eluting with chloroform/methanol (25:1) to give ethyl 2-(4-carbamoyl-1-imidazolyl)valerate (150 mg).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 3 hours at 55-60° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel (12 g) chromatography
  7. washeluting with chloroform/methanol (25:1)

Quellen und Nachweise

ORD-Eintrag
ord-a32610157fa241bfa4ddc7d1c261eb8a
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359145B1

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