GB720578A - Halogenation of steroids - Google Patents

Halogenation of steroids

Info

Publication number
GB720578A
GB720578A GB25621/52A GB2562152A GB720578A GB 720578 A GB720578 A GB 720578A GB 25621/52 A GB25621/52 A GB 25621/52A GB 2562152 A GB2562152 A GB 2562152A GB 720578 A GB720578 A GB 720578A
Authority
GB
United Kingdom
Prior art keywords
hydroxypregnane
trione
acetoxy
acyloxy
bromo
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
GB25621/52A
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 GB720578A publication Critical patent/GB720578A/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

4 - Halo - 21 - acyloxy - 17a - hydroxypregnane - 3 : 11 : 20 - triones are prepared by halogenation of 21 - acyloxy - 17a - hydroxypregnane-3 : 11 : 20-triones in tertiary butyl alcohol which may contain up to eighteen per cent of water by volume. Specified halogenating agents are chlorine, bromine, N-bromoacetamide, N - bromosuccinimide, N - chloro - succinimide, 3 - bromo - 5 : 5 - dimethyl hydantoin, 1 : 3-dibromo-5 : 5-dimethyl hydantoin, hypobromous acid and hypochlorous acid. The 21-acyloxy radicals preferably contain from one to eight carbon atoms inclusive and may carry halo, alkyl or alkoxy groups as non-reactive substituents. Traces of mineral acids expedite the reaction, which is preferably conducted below about 50 DEG C. In examples (1) 21 - acetoxy - 17a - hydroxypregnane - 3 : 11 : 20-trione in tertiary butyl alcohol containing a trace of aqueous hydrogen bromide is treated with N-bromoacetamide to produce 4-bromo - 21 - acetoxy - 17a - hydroxypregnane - 3 : 11 : 20-trione. Other examples illustrate the halogenation of the 21-acetoxy-trione using each one of the agents specified above. Further examples relate to the formation of 4-bromo-21-propionoxy-, 4 - chloro - 21 - octanoyloxy - and 4 - chloro - 21 - butanoyloxy - 17a - hydroxy - pregnane-3 : 11 : 20 - one, and many other 21 - acyloxy-4-halocompounds are listed. The required intermediate 21-acetoxy-17a -hydroxypregnane-3 : 20-trione is prepared from 3 : 17a - dihydroxypregnane - 11 : 20 - dione by bromination to yield the 21-bromo compound followed by treatment with potassium acetate in acetone, and finally oxidation with N-bromoacetamide in basic solution.
GB25621/52A 1951-10-15 1952-10-13 Halogenation of steroids Expired GB720578A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US720578XA 1951-10-15 1951-10-15

Publications (1)

Publication Number Publication Date
GB720578A true GB720578A (en) 1954-12-22

Family

ID=22105292

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25621/52A Expired GB720578A (en) 1951-10-15 1952-10-13 Halogenation of steroids

Country Status (1)

Country Link
GB (1) GB720578A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1037449B (en) * 1955-04-15 1958-08-28 Chimiotherapie Lab Franc Process for the preparation of new bromine derivatives of pregnane compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1037449B (en) * 1955-04-15 1958-08-28 Chimiotherapie Lab Franc Process for the preparation of new bromine derivatives of pregnane compounds

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