The Upjohn Co.

Alfred B Garcia

Merle G Wovcha

Leo A Kominek

Frederick J Antosz

John M Beaton

John C Knight

The subject invention concerns a novel one-stage fermentation process for making the useful steroid intermediate 9-hydroxy-3-oxo-4,17(20)-pregnadiene-20-carboxylic acid (I). This process is significantly superior to the best prior art process known for making (I).

Process of producing 9-hydroxy-3-oxo-4,17(20)-pregnadiene-20-carboxylic

Valuable steroid intermediates, 9.alpha.-hydroxyandrost-4-ene-17.beta.-ol-3-one (9.alpha.-OH testosterone), 9.alpha.-hydroxy-3-ketobisnorchol-4-en-22-ol (9.alpha.-OH BN alcohol) and 9.alpha.-hydroxy-3-ketobisnorchol-4-en-22-oic methyl ester (9.alpha.-OH BN acid methyl ester), prepared by microbiological conversion of steroids having 17-alkyl side chains of 8 to 10 carbons.

Process for preparing 9.alpha.-OH BN alcohol

Process for preparing 9.alpha.-OH BN acid methyl ester

Process for preparing 9.alpha.-OH testosterone

Valuable steroid intermediates, 9.alpha.-hydroxyandrost-4-ene-17.beta.-ol-3-one (9.alpha.--OH testosterone), 9.alpha.-hydroxy-3-ketobisnorchol-4-en-22-ol (9.alpha.--OH BN alcohol) and 9.alpha.---hydroxy-3-ketobisnorchol-4-en-22-oic methyl ester (9.alpha.--OH BN acid methyl ester), prepared by microbiological conversion of steroids having 17-alkyl side chains of 8 to 10 carbons.

Composition of matter and process

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Kalamazoo, MI, United States of America

Alfred B Garcia