Reaktionsgleichung
[C:1]([NH:4][C@H:5]([C:7]([OH:9])=O)[CH3:6])(=[O:3])[CH3:2].S(Cl)(Cl)=O.CN(C)C=O.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]([C:30]([OH:32])=[O:31])[C:23]2=[O:33].C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[C:1]([NH:4][CH:5]([CH3:6])[C:7]([NH:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]([C:30]([OH:32])=[O:31])[C:23]2=[O:33])=[O:9])(=[O:3])[CH3:2]Komponenten
Edukt 6
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 1.73 g (13.2 mmol) of N-acetyl-L-alanine, 0.97 ml (13.2 mmol) of thionyl chloride, 1.02 ml (13.02 mmol) dimethylformamide, and 50 ml of dichloromethane is stirred at -20° to -30° for 20 minutes. A mixture of 2.45 g (12 mmol) of 6-amino-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 5.04 ml (36 mmol) triethylamine, 4.57 ml (36 mmol) chlorotrimethylsilane and 100 ml of dichloromethane is stirred at room temperature for 25 minutes and is cooled to -60°. The cold acid chloride solution is added to the cold silylated quinoline and is stirred for 2 hours while the temperature comes up to 10°. The reaction mixture is evaporated to dryness and the residue is treated with water to give 2.60 g of 6-[[2-(acetylamino)-1-oxopropyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, mp 196°-200° .
Aufarbeitung
- stirringis stirred at room temperature for 25 minutes
- temperatureis cooled to -60°
- stirringis stirred for 2 hours while the temperature
- customcomes up to 10°
- customThe reaction mixture is evaporated to dryness
- additionthe residue is treated with water
Quellen und Nachweise
- ORD-Eintrag
- ord-42001e47112f4913b02a046608b59e19
- Quelldatensatz
- uspto-grants-1983_05
- Patentnummer
- US04382089
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