GB741223A - 3,20-diketo-4-bromo-11,17-dihydroxy-21-acyloxy-pregnanes and preparation of same - Google Patents

3,20-diketo-4-bromo-11,17-dihydroxy-21-acyloxy-pregnanes and preparation of same

Info

Publication number
GB741223A
GB741223A GB27629/51A GB2762951A GB741223A GB 741223 A GB741223 A GB 741223A GB 27629/51 A GB27629/51 A GB 27629/51A GB 2762951 A GB2762951 A GB 2762951A GB 741223 A GB741223 A GB 741223A
Authority
GB
United Kingdom
Prior art keywords
diketo
dihydroxy
bromo
preparation
acyloxypregnane
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
GB27629/51A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB741223A publication Critical patent/GB741223A/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 compounds of the formula <FORM:0741223/IV(a)/1> where R is an alkanoyl radical containing not more than six carbon atoms, e.g. acetyl, and the preparation thereof by reacting a D 17(20) - 3 - keto - 11 - hydroxy - 20 - cyano - 21 - acyloxy pregnene with osmium tetroxide, hydrolysing the osmate ester, e.g. with sodium sulphite and brominating the resulting 3,20-diketo-11,17-dihydroxy-21-acyloxypregnane, e.g. with bromine, to form 3,20-diketo-4-bromo-11,17-dihydroxy-21-acyloxypregnane. Subsequently said 3,20-diketo-4-bromo-11,17-dihydroxy-21-acyloxypregnane may be dehydrobrominated, e.g. by means of a semicarbazide followed by aqueous pyruvic acid, to produce D 4-3,20-diketo - 11,17 - dihydroxy - 21 - acyloxypregnene which may be hydrolysed to D 4-3,20-diketo - 11,17,21 - trihydroxypregnene. Examples describe the preparation of 3,20-diketo-4 - bromo - 11(b ), 17(a ) - dihydroxy - 21-acetoxy-pregnane and its subsequent conversion to D 4 - 3,20 - diketo - 11(b ), 17(a )-dihydroxy - 21 - acetoxy - pregnene. Specifications 741,274 and 741,276 are referred to.
GB27629/51A 1950-12-02 1951-11-26 3,20-diketo-4-bromo-11,17-dihydroxy-21-acyloxy-pregnanes and preparation of same Expired GB741223A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US741223XA 1950-12-02 1950-12-02

Publications (1)

Publication Number Publication Date
GB741223A true GB741223A (en) 1955-11-30

Family

ID=22117859

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27629/51A Expired GB741223A (en) 1950-12-02 1951-11-26 3,20-diketo-4-bromo-11,17-dihydroxy-21-acyloxy-pregnanes and preparation of same

Country Status (1)

Country Link
GB (1) GB741223A (en)

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