Dimethyl Sulfoxide → HCID 70547497, compound
Reaction equation
[CH3:1][C:2]([C@:4]1([OH:26])[C@@:8]2([CH3:25])[CH2:9][CH2:10][C@@H:11]3[C@:22]4([CH3:23])[C:15](=[CH:16][C:17]([C@H:19]5[C@@H:21]4[CH2:20]5)=[O:18])[C:14]([Cl:24])=[CH:13][C@H:12]3[C@@H:7]2[CH2:6][CH2:5]1)=[O:3].CS(C)=[O:29]>>[Cl:24][C:14]1[C:15]2[C@:22]([CH3:23])([C@H:21]3[CH2:20][C@H:19]3[C:17](=[O:18])[CH:16]=2)[C@@H:11]2[C@H:12]([C@H:7]3[C@:8]([CH3:25])([CH2:9][CH2:10]2)[C@@:4]([OH:26])([C:2](=[O:3])[CH3:1])[CH2:5][C@H:6]3[OH:29])[CH:13]=1Participants
Procedure
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.
Workup
- customUnder the culturing and fermentation conditions of Example 1, a 50-liter fermentor is prepared with 28 l
- customafter a culture period of 12 hours
- extractionAfter a contact period of 60 hours, the content of the fermentor is extracted with methyl isobutyl ketone
- customThe thus-obtained crude product
- customis chromatographed over a silica gel column with the use of the solvent gradient methylene chloride-methylene chloride/acetone
- customrecrystallized from acetone/hexane
Sources & evidence
- ORD record
- ord-5528cfc569b046f2a94de8e9c64a10c0
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04196204
Reaction notes
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