GB726807A - Simultaneous oxidation and halogenation of steroids - Google Patents

Simultaneous oxidation and halogenation of steroids

Info

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
Application number
GB24612/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB726807A publication Critical patent/GB726807A/en
Expired legal-status Critical Current

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.
GB24612/52A 1951-10-03 1952-10-01 Simultaneous oxidation and halogenation of steroids Expired GB726807A (en)

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)

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