Reaktion #1244136

Reaktionsgleichung

cyproterone

dimethyl sulfoxide

→

6-chloro-15β,17-dihydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione

Ausbeute 36.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeUnder the culturing and fermentation conditions of Example 1, a 50-liter fermentor is prepared with 28 l
2. 2
   Sonstigeafter a culture period of 12 hours
3. 3
   ExtraktionAfter a contact period of 60 hours, the content of the fermentor is extracted with methyl isobutyl ketone
4. 4
   SonstigeThe thus-obtained crude product
5. 5
   Sonstigeis chromatographed over a silica gel column with the use of the solvent gradient methylene chloride-methylene chloride/acetone
6. 6
   Sonstigerecrystallized from acetone/hexane

Vorschrift

Under the culturing and fermentation conditions of Example 1, a 50-liter fermentor is prepared with 28 l. of a Bacillus megaterium culture and, after a culture period of 12 hours, combined with 6 g. of cyproterone (6-chloro-17-hydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione), dissolved in 400 ml. of dimethyl sulfoxide. After a contact period of 60 hours, the content of the fermentor is extracted with methyl isobutyl ketone and worked up as described in Example 1. The thus-obtained crude product is chromatographed over a silica gel column with the use of the solvent gradient methylene chloride-methylene chloride/acetone and recrystallized from acetone/hexane, thus obtaining in a 36% yield pure 6-chloro-15β,17-dihydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione, m.p. 251°-253° C.

Quelle