HCID 178418840, Verbindung → 12a-Deoxytetracycline
Reaktionsgleichung
[CH3:1][C@:2]1([OH:32])[C@@H:16]2[C:11](=[C:12]([OH:30])[C@:13]3(O)[C:20](=[O:21])[C:19]([C:22]([NH2:24])=[O:23])=[C:18]([OH:25])[C@@H:17]([N:26]([CH3:28])[CH3:27])[C@@H:14]3[CH2:15]2)[C:9](=[O:10])[C:8]2[C:7]([OH:31])=[CH:6][CH:5]=[CH:4][C:3]1=2>N.[Zn]>[CH3:1][C:2]1([OH:32])[C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([OH:31])[C:8]=2[C:9]([OH:10])=[C:11]2[CH:16]1[CH2:15][CH:14]1[CH:17]([N:26]([CH3:28])[CH3:27])[C:18]([OH:25])=[C:19]([C:22]([NH2:24])=[O:23])[C:20](=[O:21])[CH:13]1[C:12]2=[O:30]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution was prepared by dissolving 2 g of tetracycline in 50 ml of a 15% aqueous ammonia solution. To the resulting solution 4 g of zinc dust was added and the mixture was vigorously stirred. After being stirred for two (2) hours, the reaction mixture was filtered to remove excess zinc dust. The filtrate was neutralized with concentrated hydrochloric acid under ice-cooling. The precipitated solid was collected by filtration and then mixed with 450 ml of water. The mixture was adjusted to a pH of 1.8 by use of hydrochloric acid. The solution obtained was extracted with ether by liquid-liquid extraction method. The extract was concentrated to give 450 mg of crude product, which was recrystallized from dimethylformamide-methanol to yield 400 mg of 12a-deoxytetracycline (yield: 21%). HPLC revealed that this product was a mixture of two types of isomers, molecular weight FD mass [M]+ 428.