N-Iodosuccinimide → HCID 54687146, Verbindung
Reaktionsgleichung
[CH3:1][N:2]([C@@H:4]1[C:23]([OH:24])=[C:22]([C:25]([NH2:27])=[O:26])[C:20](=[O:21])[C@:19]2([OH:28])[C@H:5]1[CH2:6][C@H:7]1[C:17](=[C:18]2[OH:29])[C:15](=[O:16])[C:14]2[C:13]([OH:30])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)[CH3:3].[I:31]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[CH3:3][N:2]([C@@H:4]1[C:23](=[O:24])[C:22]([C:25]([NH2:27])=[O:26])=[C:20]([OH:21])[C@:19]2([OH:28])[C@H:5]1[CH2:6][C@H:7]1[C:17]([C:18]2=[O:29])=[C:15]([OH:16])[C:14]2[C:9](=[C:10]([I:31])[CH:11]=[CH:12][C:13]=2[OH:30])[CH2:8]1)[CH3:1]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Five grams of sancycline was dissolved in 85 mL of concentrated sulfuric acid that was cooled to 0° C. (on ice). N-iodosuccinimide (NIS) was added to the reaction in 300 mg portions every 15 minutes and reacted for 5 hours. The reaction is removed from the ice bath. The mixture, analyzed by HPLC or TLC, show the product of D-ring iodotetracyclines. After the reaction was complete, the sulfuric acid was dripped slowly 1 L of ice water and extracted 7 times with 300 mL of n-butanol. The solvent was removed in vacuo to produce a mixture of three products. The 7-iodo regioisomer, 9-regioisomer and 7,9-diiodosancycline derivative of sancycline were purified by preparative HPLC chromatography or by methods known in the art.