Sodium Carbonate → methyl 5-(N-hydroxycarbamimidoyl)pentanoate

HRID 1039186

Reaktionsgleichung

Reaktionsgleichung von HRID 1039186
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][O:8][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15].Cl.[NH2:18][OH:19]>C(O)C>[OH:19][NH:18][C:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]([O:8][CH3:7])=[O:16])=[NH:15]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 554130Methyl 5-cyanopentanoate

Produkt 1

HCID 178500328methyl 5-(N-hydroxycarbamimidoyl)pentanoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Add sodium carbonate (4.5 g, 42 mmol) to a solution of commercially available 5-cyano-pentanoic acid methyl ester (5.0 g, 35 mmol) and hydroxylamine hydrochloride (2.9 g, 42 mmol) in ethanol (100 mL) at room temperature under nitrogen and heat the mixture at reflux for 5.5 h. Filter the mixture through celite and remove the solvent under reduced pressure to provide crude methyl 5-(N-hydroxycarbamimidoyl)pentanoate (5.3 g, 87% yield), which is carried forward without further purification.

Aufarbeitung

  1. temperatureheat the mixture
  2. temperatureat reflux for 5.5 h
  3. filtrationFilter the mixture through celite
  4. customremove the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7e662e83efbc49e9b4a38efd8381f4ea
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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