Pyridine → Ethyl 3-[(cyclopentylcarbonyl)amino]-2-oxopentanoate

HRID 1791181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1791181
[CH:1]1([C:6]([NH:8][CH:9]([CH2:13][CH3:14])[C:10]([OH:12])=O)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.ClC(=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1>[CH:1]1([C:6]([NH:8][CH:9]([CH2:13][CH3:14])[C:10](=[O:12])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 219912592-[(Cyclopentylcarbonyl)amino]butanoic acid

Produkt 1

HCID 21991319Ethyl 3-[(cyclopentylcarbonyl)amino]-2-oxopentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.6 g (8 mmol) 2-[(cyclopentylcarbonyl)amino]butanoic acid are suspended in 30 ml tetrahydrofuran and heated to reflux together with 1.91 g (24 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 2.19 g (16 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at reflux until no more evolution of gas can be observed. After cooling down to room temperature, the reaction mixture is added to ice water and the organic phase extracted with ethyl acetate. The dried organic phase is evaporated to dryness in vacuo, dissolved in ethanol and the solution directly used for the next reaction.

Aufarbeitung

  1. temperatureheated
  2. temperatureWhile heating
  3. temperatureat reflux
  4. temperatureThe reaction mixture is heated
  5. temperatureat reflux until no more evolution of gas
  6. extractionthe organic phase extracted with ethyl acetate
  7. customThe dried organic phase is evaporated to dryness in vacuo
  8. dissolutiondissolved in ethanol
  9. customthe solution directly used for the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-2a59515024644f7f9268fc7d7abe72fa
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074790B2

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