Dimethyl Sulfoxide → 7alpha-Hydroxytestosterone

HRID 27207

Reaction equation

HRID 27207 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.CS(C)=[O:24]>>[OH:24][C@@H:9]1[CH2:10][C:11]2[C@:16]([CH3:17])([CH2:15][CH2:14][C:13](=[O:21])[CH:12]=2)[C@@H:18]2[C@@H:8]1[C@H:5]1[C@@:3]([CH2:20][CH2:19]2)([CH3:4])[C@@H:2]([OH:1])[CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 6013Testosterone

Product 1

HCID 655417alpha-Hydroxytestosterone

Conditions

Temperature
26.5 °C

Procedure

100 ml of the medium of Example 1 were inoculated with Mucor hiemalis FERM P-3800 and shaken at 26.5° C. for 22 hours. The culture was then treated with 50 mg of 17β-hydroxy-4-androsten-3one in 1 ml of dimethyl sulphoxide and incubated for 8 days. There were obtained from the culture filtrate 4.8 mg of 7α,17β-dihydroxy-4-androsten-3-one of melting point 191°-193° C.

Workup

  1. waitincubated for 8 days

Sources & evidence

ORD record
ord-66649ce96602436f818ee91f78ecfcf8
Source dataset
uspto-grants-1980_09
Patent number
US04220716

Linked notes

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