CH293816A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH293816A
CH293816A CH293816DA CH293816A CH 293816 A CH293816 A CH 293816A CH 293816D A CH293816D A CH 293816DA CH 293816 A CH293816 A CH 293816A
Authority
CH
Switzerland
Prior art keywords
preparation
new ester
diketo
deoxycorticosterone
diazo
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH293816A publication Critical patent/CH293816A/en

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung     eines    neuen     Esters.       Die vorliegende Erfindung betrifft ein  Verfahren zur Herstellung des     Trimethyl-          acetats    von     Desoxycorticosteron.     



  Der neue Ester wird erhalten, wenn     man     das     d4-3,20-Diketo-21-diazo-pregnen    mit     Tri-          met.hy        lessigsäiire        umsetzt.    Das     Verfahrens-          produkt,    das     Trimethylacetat    von     Desoxycor-          ticosteron,    schmilzt bei 199 bis 200 . Es soll  als Heilmittel verwendet. werden.  



  Die     Umsetzung    mit     Trimethy        lessigsäure     kann in An- oder Abwesenheit von Verdün  nungsmitteln, vorteilhaft bei erhöhter     Tempe-          ;-atiii#.    durchgeführt werden.  



       Beispiel:     3 Gewichtsteile     d4-3,20-Diketo-21=diazo-          hregnen    werden mit 12 Gewichtsteilen     Tri-          methyiessigsäure    versetzt und in einem Ölbad  bis zur beginnenden     Stickstoffente;        icklung    er  wärmt. Die Stickstoffabspaltung     setzt    bei  etwa     135 <     ein und wird bei 150  sehr heftig.  Nach beendeter     Stickstoffentwicklung    und  Abkühlen versetzt man mit     Äther    und wäscht  mit verdünnter     Sodalösung    und Wasser.

   Der  Rückstand der getrockneten und     eingedampf-          ten        ätherischen    Lösung wird aus einem Ge-    misch von Benzol und     Isopropyläther        kristal-          lisiert.    Man erhält das     Desoxyeorticosteron-          trimethyIacetat.    der Formel  
EMI0001.0042     
    F. =<B>199</B> bis 200 ;     [a]    i, = + l76  (c = 1,035  in Chloroform).  



  Das als Ausgangsstoff     verwendete        J1-3,        20-          Diketo-21-dia.zo-pregnen    lässt sich durch Oxy  dation des bekannten     A5-3-Oxy-20-keto-21-di-          -pregnens    nach     Oppenauer    mit     Cyclohexa-          ,        -)zo          non    und     Aluminiumisopropylat    in     Toluol     herstellen.



  Process for the preparation of a new ester. The present invention relates to a process for the preparation of the trimethyl acetate of deoxycorticosterone.



  The new ester is obtained when the d4-3,20-diketo-21-diazo-pregnene is reacted with trimet.hy lessetic acid. The process product, the trimethyl acetate of deoxycorticosterone, melts at 199 to 200. It is said to be used as a remedy. will.



  The reaction with Trimethy lessigsäure can in the presence or absence of diluents, advantageous at increased Tempe; -atiii #. be performed.



       Example: 3 parts by weight of d4-3,20-Diketo-21 = diazo- hregnen are mixed with 12 parts by weight of trimethylacetic acid and put in an oil bath until the nitrogen duck begins; winding it warms. The elimination of nitrogen begins at about 135 <and becomes very violent at 150. After the evolution of nitrogen has ended and cooling is complete, ether is added and the mixture is washed with dilute soda solution and water.

   The residue of the dried and evaporated ethereal solution is crystallized from a mixture of benzene and isopropyl ether. The deoxyeorticosterone trimethyl acetate is obtained. the formula
EMI0001.0042
    F. = 199 to 200; [a] i, = + 176 (c = 1.035 in chloroform).



  The J1-3, 20-diketo-21-dia.zo-pregnen used as starting material can be oxidized by the well-known A5-3-oxy-20-keto-21-di- pregnen according to Oppenauer with cyclohexa-, -) zo non and aluminum isopropylate in toluene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung , eines neuen Esters, dadurch gekennzeichnet, dass man das 94-3,20-Diketo-21-diazo-pregnen mit Trime- thylessigsätire umsetzt. Das Verfahrenspro dukt, das Trimethylacetat von Desoxycortico- steron, schmilzt. bei 199 bis 200 . PATENT CLAIM: Process for the production of a new ester, characterized in that the 94-3,20-diketo-21-diazo-pregnene is reacted with trimethyl acetic acid. The process product, the trimethyl acetate of deoxycorticosterone, melts. at 199 to 200.
CH293816D 1950-03-24 1950-03-24 Process for the preparation of a new ester. CH293816A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH293816T 1950-03-24

Publications (1)

Publication Number Publication Date
CH293816A true CH293816A (en) 1953-10-15

Family

ID=4488321

Family Applications (1)

Application Number Title Priority Date Filing Date
CH293816D CH293816A (en) 1950-03-24 1950-03-24 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH293816A (en)

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