Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:12])[C@:4]([N:9]=[C:10]=[O:11])([CH:6]([CH3:8])[CH3:7])N.[CH2:13]([N:15]([C:18]1[S:19][CH:20]=[C:21]([CH2:23][OH:24])[N:22]=1)[CH2:16][CH3:17])[CH3:14]>ClCCl.CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH:9][C:10]([O:24][CH2:23][C:21]1[N:22]=[C:18]([N:15]([CH2:16][CH3:17])[CH2:13][CH3:14])[S:19][CH:20]=1)=[O:11]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
A solution of 5.11 mmol of α-isocyanato-valine methyl ester in 10 ml of dichloromethane was treated with 0.864 g (4.65 mmol) of 2-(N,N-diethylamino)-4-(hydroxymethyl)thiazole and 0.46 mmol of 4-dimethylaminopyridine. The resulting solution was stirred at ambient temperature for 16 h, after which it was diluted with 200 ml of chloroform, washed successively with 10% citric acid, aqueous NaHCO3, and saturated brine. After drying over Na2SO4, the solvent was removed in vacuo, and the residue was chromatographed on silica gel using 1-2% methanol in chloroform to provide 1.31 g (82%) of the desired compound, Rf 0.51 (4% methanol in chloroform) as an oil. 1H NMR (CDCl3) δ0.89 (d, J=7 Hz, 3H), 0.96 (d, J=7 Hz, 3H), 1.24 (t, J=7 Hz, 6H), 2.15 (m, 1H), 3.51 (q, J=7 Hz, 4H), 3.74 (s, 3H), 4.29 (dd, J=8, 4 Hz, 1H), 5.03 (s, 2H), 5.34 (br d, J=8 Hz, 1H), 6.42 (s, 1H). Mass spectrum: (M+H)+ =344.
Aufarbeitung
- washwashed successively with 10% citric acid, aqueous NaHCO3, and saturated brine
- dry with materialAfter drying over Na2SO4
- customthe solvent was removed in vacuo
- customthe residue was chromatographed on silica gel using 1-2% methanol in chloroform
Quellen und Nachweise
- ORD-Eintrag
- ord-626a00d81aa445ff8f01adeee3e42e4c
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05616720
Verknüpfte Notizen
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