GB726807A - Simultaneous oxidation and halogenation of steroids - Google Patents
Simultaneous oxidation and halogenation of steroidsInfo
- Publication number
- GB726807A GB726807A GB24612/52A GB2461252A GB726807A GB 726807 A GB726807 A GB 726807A GB 24612/52 A GB24612/52 A GB 24612/52A GB 2461252 A GB2461252 A GB 2461252A GB 726807 A GB726807 A GB 726807A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxypregnane
- acetoxy
- dimethylhydantoin
- trione
- dione
- 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
The invention comprises 4-chloro-21-acyloxy-17a - hydroxypregnane - 3 : 11 : 20 - triones wherein the acyloxy group is derived from an aliphatic carboxylic acid containing from one to eight carbon atoms inclusive, and a process for the concurrent oxidation and halogenation of a 21 - acyloxy - 3 : 17a - dihydroxypregnane - 11 : 20 - dione to yield a 4 - halo - 21 - acyloxy - 17a -hydroxypregnane- 3 : 11 : 20-trione which comprises reacting the dione with N-bromoacetamide, N-bromosuccinimide, N-chlorosuccinimide, 3 - bromo -5 : 5 - dimethylhydantoin or 1 : 3 - dibromo - 5 : 5 - dimethylhydantoin in an inert solvent, preferably at a temperature between 15 DEG and 40 DEG C. Specified solvents are dioxane and tertiary alkanols; tertiary butanol, containing water from traces to about 18 per cent by volume being preferred. In examples: (1) 21 - acetoxy - 3a ,17a - dihydroxypregnane - 11 : 20-dione in aqueous tertiary butyl alcohol is treated with N-bromacetamide to give 4-bromo - 21 - acetoxy - 17a - hydroxypregnane - 3 : 11 : 20-trione; (2) similar treatment with N-chlorsuccinimide yields 4 - chloro - 21 - acetoxy-17a - hydroxypregnane - 3 : 11 : 20 - trione. Other examples repeat (1) replacing N-bromacetamide by 3-bromo-5 : 5-dimethylhydantoin; 1 : 3 - dibromo - 5 : 5 - dimethylhydantoin and N-bromsuccinimide; (3) 21-acetoxy-3b : 17a -dihydroxypregnane-11 : 20-dione is treated with N-bromacetamide to yield 4-bromo-21-acetoxy-17a - hydroxypregnane - 3 : 11 : 20 - trione. Further examples of 4-halo compounds in which the 21-acyloxy group is formyloxy and propionoxy to octanoyloxy are listed.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US726807XA | 1951-10-03 | 1951-10-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB726807A true GB726807A (en) | 1955-03-23 |
Family
ID=22109137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24612/52A Expired GB726807A (en) | 1951-10-03 | 1952-10-01 | Simultaneous oxidation and halogenation of steroids |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB726807A (en) |
-
1952
- 1952-10-01 GB GB24612/52A patent/GB726807A/en not_active Expired
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