GB630076A - Manufacture of intermediates in the synthesis of adrenal cortical hormone - Google Patents
Manufacture of intermediates in the synthesis of adrenal cortical hormoneInfo
- Publication number
- GB630076A GB630076A GB21046/46A GB2104646A GB630076A GB 630076 A GB630076 A GB 630076A GB 21046/46 A GB21046/46 A GB 21046/46A GB 2104646 A GB2104646 A GB 2104646A GB 630076 A GB630076 A GB 630076A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diketo
- hydroxy
- bromine
- ether
- isolated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
4-Bromo-3 : 11-diketo-17(b )-hydroxy-20 : 21-diacyloxypregnanes (in which the acyl groups preferably correspond to an aliphatic acid containing not more than 6 carbon atoms in the molecule) are manufactured by treating a 3 : 11 - diketo - 17(b ) - hydroxy - 20 : 21 - diacyloxy pregnane with a substantially equimolecular proportion of bromine, preferably in an inert solvent. The product may be isolated by dissolving the reaction mixture in ether, washing with dilute alkali or alkali meta carbonate solution, evaporating to dryness in vacuo and recrystallizing from ether, and may be treated with a tertiary base to produce a D 4,5-3 : 11-diketo-17(b )-hydroxy-20 : 21-diacyloxypregnene, which on hydrolysis yields D 4,5-3 : 11-diketo-17(b ) : 20 : 21-trihydroxypregnene. In an example, 3 : 11-diketo-17(b )-hydroxy-20 : 21-diacetoxypregnane is treated with bromine in glacial acetic acid, and the resulting 4-bromo derivative is isolated and refluxed in pyridine to form D 4,5 - 3 : 11 - diketo - 17(b ) - hydroxy -20 : 21-diacetoxypregnene, from which the trihydroxy compound may be produced by hydrolysis with an aqueous methanolic solution of potassium carbonate and bicarbonate. Additional starting materials specified are those in which the acyl groups are those of propionic, butyric, valeric, caproic, capric, benzoic, toluic and phenylacetic acids. Specification 628,255 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US630076XA | 1945-07-14 | 1945-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB630076A true GB630076A (en) | 1949-10-05 |
Family
ID=22046274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21046/46A Expired GB630076A (en) | 1945-07-14 | 1946-07-13 | Manufacture of intermediates in the synthesis of adrenal cortical hormone |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB630076A (en) |
-
1946
- 1946-07-13 GB GB21046/46A patent/GB630076A/en not_active Expired
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