Process for degrading the 20-carboxyl group of .DELTA.4-Steroid-

Details Process for degrading the 20-carboxyl group of .DELTA.4-Steroid- Process for degrading the 20-carboxyl group of .DELTA.4-Steroid-

1982-08-13

1984-05-01

Roberts, Elbert L.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603971, 2603974, 2603973, C07J 500

Patent

active

044460724

ABSTRACT:
.DELTA.4-Steroid-20-carboxylic acids (BNC compounds) which may optionally contain at least one other double bond in the 1(2)- and/or 9(11)-position and which may also contain an oxygen function, particularly a hydroxyl group or a keto group, in the 11-position, are degraded in the 20-carboxyl group by carboxy inversion degradation. To achieve this, the BNC-carboxylic acids are first transformed into their acid halides which are reacted with peracids to form mixed acid anhydrides, followed by hydrolysis. The reaction product obtained is a mixture of 20-hydroxy- and 20(21)-ene-steroid compounds which contain one carbon atom less than the starting material used. New and known C21-steroid compounds can be produced by the process. The C21-steroid compounds having an oxygenated function in the 11-position may be processed to prednisolone and prednisone by known procedures.

REFERENCES:
patent: 4072710 (1978-02-01), Coll
patent: 4255345 (1981-03-01), Krbechek
Chemical Abstracts (1982), vol. 96 Par. 143171z.

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