Ethyl Acetate → 3-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

HRID 467744

Reaktionsgleichung

Reaktionsgleichung von HRID 467744
[CH:1]1([NH:4][C:5](=[O:10])[C:6](Cl)=[N:7][OH:8])[CH2:3][CH2:2]1.[CH2:11]([O:13][C:14](=[O:20])/[CH:15]=[CH:16]/N(C)C)[CH3:12].C(OCC)(=O)C>C1COCC1>[CH2:11]([O:13][C:14]([C:15]1[C:6]([C:5](=[O:10])[NH:4][CH:1]2[CH2:3][CH2:2]2)=[N:7][O:8][CH:16]=1)=[O:20])[CH3:12]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 5369162Ethyl trans-3-dimethylaminoacrylateHCID 85344446N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide

Produkt 1

HCID 700979003-(Cyclopropylcarbamoyl)-isoxazole-4-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of N-cyclopropyl-2-chloro-2-hydroxyimino-acetamide (2 g, 12.3 mmol) and (E)-3-(dimethylamino)-acrylic acid ethyl ester (1.76 ml, 12.3 mmol) in THF (25 ml) was heated at 75° C. for 2 h. The reaction was then cooled to r.t., poured into 100 mL ethyl acetate and extracted with 1 M HCl. The aqueous layers were back-extracted with ethyl acetate. The organic phase was washed with water and brine, dried and evaporated. The product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (1.6 g, 58%).

Aufarbeitung

  1. temperatureThe reaction was then cooled to r.t.
  2. extractionextracted with 1 M HCl
  3. extractionThe aqueous layers were back-extracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. customdried
  6. customevaporated
  7. customThe product was obtained
  8. customafter purification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-495a9bd1d11a4de7a97999cd4bc09afd
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

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