N-methylpent-4-en-1-amine → Methyl 3-methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valinate

HRID 1511560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511560
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].[CH3:8][C:9]([CH3:19])([CH3:18])[C@@H:10]([C:14]([O:16][CH3:17])=[O:15])[N:11]=[C:12]=[O:13]>O1CCCC1>[CH3:8][C:9]([CH3:19])([CH3:18])[C@@H:10]([C:14]([O:16][CH3:17])=[O:15])[NH:11][C:12]([N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7])=[O:13]

Komponenten

4

Edukt 2

HCID 541660N-methylpent-4-en-1-amineHCID 59856496methyl (2S)-2-isocyanato-3,3-dimethylbutanoate

Produkt 1

HCID 59856469Methyl 3-methyl-N-[methyl(pent-4-en-1-yl)carbamoyl]-L-valinateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of N-methylpent-4-en-1-amine (2.0 g, 20.2 mmol) in tetrahydrofuran (20 mL) was stirred at room temperature under nitrogen. To this was added methyl 3-methyl-N-(oxomethylene)-L-valinate (3.5 g, 20.2 mmol) and the resulting solution stirred 2 h. Contents of the reaction flask were evaporated and subjected to flash column chromatography eluting with hexane/ethyl acetate 60/40 to give methyl 3-Methyl-N-{[methyl(pent-4-enyl)amino]carbonyl}-L-valinate as an orange oil, 3.02 g (55% yield).

Aufarbeitung

  1. customContents of the reaction flask were evaporated
  2. washeluting with hexane/ethyl acetate 60/40

Quellen und Nachweise

ORD-Eintrag
ord-3df303074a3c4828970d44f9cfff4acc
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216999B2

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