Reaktionsgleichung
[CH3:1][N:2]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][OH:10])[N:8]=1)[CH3:3].[CH3:11][O:12][C:13](=[O:22])[C@:14]([N:19]=[C:20]=[O:21])([CH:16]([CH3:18])[CH3:17])N>CN(C)C1C=CN=CC=1.ClCCl>[CH3:11][O:12][C:13](=[O:22])[C@H:14]([CH:16]([CH3:17])[CH3:18])[NH:19][C:20]([O:10][CH2:9][C:7]1[N:8]=[C:4]([N:2]([CH3:3])[CH3:1])[S:5][CH:6]=1)=[O:21]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 505 mg (3.19 mmol) of 2-(N,N-dimethylamino)-4-(hydroxymethyl)thiazole, 3.19 mmol of α-isocyanato-L-valine methyl ester, and 100 mg of 4-dimethylaminopyridine in 30 ml of dichloromethane was heated at reflux for 3 h. The resulting solution was allowed to cool, diluted with dichloromethane, washed sequentially with 10% citric acid, aqueous Na2CO3, and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography using 2% methanol in chloroform to provide 0.95 g (95%) of the desired compound, Rf 0.42 (4% methanol in chloroform). 1H NMR (CDCl3), δ0.84 (d, J=7 Hz, 3H), 0.93 (d, J=7 Hz, 3H), 2.12 (m, 1H), 3.11 (s, 6H), 3.73 (s, 3H), 4.24 (dd, J=8, 4 Hz, 1H), 4.99 (s, 2H), 5.26 (br d, 1H), 6.49 (s, 1H). Mass spectrum: (M+H)+ =316.
Aufarbeitung
- temperatureat reflux for 3 h
- temperatureto cool
- washwashed sequentially with 10% citric acid, aqueous Na2CO3, and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-213c0e66afd44892b1b156d8ca7ab8f2
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05616720
Verknüpfte Notizen
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