Reaktion #708900

Reaktionsgleichung

daunorubicin

ethyl acetylacetate

toluene acetone

→

N-(1-carboethoxy-propen-1-yl-2)-daunorubicin

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution is then evaporated until a small volume of composition
2. 2
   workup.ADDITIONthe final product is pecipitated by the addition of a mixture of ethyl ether and hexane in a ratio of 1:1
3. 3
   SonstigeThe precipitated results from the mixture of acetone and ethyl ether

Vorschrift

0.53 gram of daunorubicin in a free base is dissolved in 100 ml of methylene chloride. 1 ml of ethyl acetylacetate is added to the solution by constant stirring. The entire mixture is agitated for 12 hours at room temperature in a nitrogenic atmosphere. The reaction is checked by means of thin-layer chromatography on a silica gel in a toluene-acetone system in a ratio of 8:1. The solution is then evaporated until a small volume of composition remains and, the final product is pecipitated by the addition of a mixture of ethyl ether and hexane in a ratio of 1:1. The precipitated results from the mixture of acetone and ethyl ether. 0.4 g of N-(1-carboethoxy-propen-1-yl-2)-daunorubicin is obtained which corresponds to 60 percent of the theoretical yield. The composition decomposes at 151°-154° C., M.S.F.D. m/z 639 (M+, 80 percent of relative intensity); 640 (M+ +1, 100 percent of relative intensity); IR (KBr)ν=1590, 1610, 1650, 1670, 1715, 1720, cm-1 (chelate and free carbonyl groups).

Quelle