Potassium Carbonate → methyl-(R)-4-(1-carbamoylpropylamino)butyrate

HRID 2197660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197660
Br[C@@H:2]([CH2:6][CH3:7])[C:3]([NH2:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:15][O:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][NH2:21]>C(#N)C>[CH3:15][O:16][C:17](=[O:22])[CH2:18][CH2:19][CH2:20][NH:21][C@@H:2]([C:3](=[O:4])[NH2:5])[CH2:6][CH3:7]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 51414846(S)-2-bromobutyramide

Produkt 1

HCID 59650081methyl-(R)-4-(1-carbamoylpropylamino)butyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of (S)-2-bromobutyramide (IIh) (optical purity>98.4%; 0.25 g, 1.5 mmol), potassium carbonate (1.1 g, 8.0 mmol, 5 equiv.) and methyl-4-aminobutyrate hydrochloride (0.46 g, 3.0 mmol, 2 equiv.) is diluted in 5 ml (15 vol.) of acetonitrile and heated at 60° C. for until complete conversion. After 43 hours (GC: >90% conversion), the mixture is cooled to room temperature and filtered. The cake is rinsed with acetonitrile (20 ml) and the combined filtrates are concentrated to dryness under reduce pressure. The crude product is used directly in the subsequent step.

Aufarbeitung

  1. temperaturethe mixture is cooled to room temperature
  2. filtrationfiltered
  3. washThe cake is rinsed with acetonitrile (20 ml)
  4. concentrationthe combined filtrates are concentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b518c0eaa8d34c00a317dac27ef069c7
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338621B2

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