CH296567A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH296567A
CH296567A CH296567DA CH296567A CH 296567 A CH296567 A CH 296567A CH 296567D A CH296567D A CH 296567DA CH 296567 A CH296567 A CH 296567A
Authority
CH
Switzerland
Prior art keywords
preparation
new ester
pregnen
formula
diketo
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 CH296567A publication Critical patent/CH296567A/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     21-Trimethyl-          acetats    von d 4-3,20-Diketo-llss,17a,21-t.rioxy-         pregnen.       Der neue Ester wird erhalten, wenn man  ein d     4-3,20-Diketo-11ss,17a-dioxy-pregnen    der  Formel  
EMI0001.0008     
    mit einer Verbindung der Formel       (C113)        sC-CO-Y          umsetzt,

      wobei X und Y bei der Reaktion sich  mit Ausnahme eines in einem von ihnen     ent-          lialtenen    Sauerstoffatoms abspaltende Reste  bedeuten. Das Verfahrensprodukt, das 4 4  3.20 -     Diketo        -11ss,17a    -     dioxy    - 21-     trimethplacet-          oxy-pre\,nen,    schmilzt zwischen 240 und 260  C  unter Zersetzung. Es soll als Heilmittel ver  wendet werden.  



  Im Ausgangsstoff der oben angegebenen  Formel kann X zum Beispiel eine     Oxygruppe     sein, die bei der Umsetzung mit     Trimethyl-          essigsäure    oder einem reaktionsfähigen Deri  vat davon, wie einem     Halogenid,    einem. Ester  oder dem     Anhydrid,    in An- oder Abwesenheit  eines Kondensationsmittels, die Trimethylacet-         oxygruppe    ergibt. Ferner kann der genannte       Substituent    in     21-Stellung    eine veresterte       Oxy        gruppe,    z.

   B. ein Halogenatom, darstellen,  das bei der     Behandlung    mit     Trimethylessig-          säure    oder einem Salz davon die     Trimethyl-          acetoxygruppe    liefert.

      <I>Beispiel:</I>    Zu einer Lösung von 9,5 Gewichtsteilen       44-3,20-Diketo-llss,17a,21-trioxy-pregnen    in  20     Volumteilen        Pyridin    gibt man unter Rüh  ren und Eiskühlung<B>8,5</B>     Volumteile        Trimethyl-          aeetylchlorid.    Die Reaktionslösung wird wäh  rend 15 Stunden bei -10  C stehen gelassen  und dann unter Eiskühlung mit Eis     und    Was  ser versetzt.

   Das ausgefällte d     4-3,20-Diketo-          11ss,17a@-dioxy-21-trimethylaeetoxy    -     pregnen     der Formel  
EMI0001.0044     
    wird     abfiltriert    und mit Wasser gewaschen.  Nach     Umkristallisieren    aus Aceton schmilzt es  zwischen 240 und 260  C unter Zersetzung.



      Process for the preparation of a new ester. The present invention relates to a process for the preparation of the 21-trimethyl acetate of d 4-3,20-diketo-llss, 17a, 21-t.rioxy-pregnen. The new ester is obtained if one ad 4-3,20-diketo-11ss, 17a-dioxy-pregnen of the formula
EMI0001.0008
    with a compound of the formula (C113) reacts sC-CO-Y,

      where X and Y denote radicals which split off during the reaction with the exception of one of the oxygen atoms released from them. The product of the process, the 4 4 3.20 - diketo -11ss, 17a - dioxy - 21-trimethplacetoxy-pre \, nen, melts between 240 and 260 C with decomposition. It is intended to be used as a remedy.



  In the starting material of the formula given above, X can be, for example, an oxy group, which in the reaction with trimethyl acetic acid or a reactive derivative thereof, such as a halide, a. Ester or the anhydride, in the presence or absence of a condensing agent, which gives the trimethylacetoxy group. Furthermore, said substituent in the 21-position can be an esterified oxy group, e.g.

   B. represent a halogen atom, which on treatment with trimethyl acetic acid or a salt thereof gives the trimethyl acetoxy group.

      <I> Example: </I> To a solution of 9.5 parts by weight of 44-3,20-diketo-llss, 17a, 21-trioxy-pregnen in 20 parts by volume of pyridine are added with stirring and ice cooling <B> 8, 5 parts by volume of trimethyl aeetyl chloride. The reaction solution is left to stand for 15 hours at -10 C and then ice and water are added while cooling with ice.

   The precipitated d 4-3,20-diketo-11ss, 17a @ -dioxy-21-trimethylaeetoxy - pregnen the formula
EMI0001.0044
    is filtered off and washed with water. After recrystallization from acetone, it melts between 240 and 260 C with decomposition.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Esters, dadurch gekennzeichnet, dass man ein d4-3,20-Dilieto-11ss,17a-dioxy-pregnen der Formel EMI0002.0002 mit einer Verbindung der Formel (CH3) 3C-CO-Y umsetzt, wobei X und Y bei der Reaktion sich mit Ausnahme eines in einem von ihnen ent haltenen Sauerstoffatoms abspaltende Reste bedeuten. Das Verfahrensprodukt, das 4 4 3,20 -Diketo -11ss,17a - dioxy - 21- trimethylacet- oxy-pregnen, schmilzt zwischen 240 und 260 C unter Zersetzung. PATENT CLAIM: Process for the preparation of a new ester, characterized in that a d4-3,20-Dilieto-11ss, 17a-dioxy-pregnen of the formula EMI0002.0002 with a compound of the formula (CH3) 3C-CO-Y, where X and Y are radicals which are split off in the reaction, with the exception of one of them containing oxygen atoms. The product of the process, the 4 4 3,20 -diketo -11ss, 17a-dioxy-21-trimethylacetoxy-pregnen, melts between 240 and 260 C with decomposition.
CH296567D 1950-03-24 1950-03-24 Process for the preparation of a new ester. CH296567A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH296567T 1950-03-24
CH293297T 1950-03-24

Publications (1)

Publication Number Publication Date
CH296567A true CH296567A (en) 1954-02-15

Family

ID=25733340

Family Applications (1)

Application Number Title Priority Date Filing Date
CH296567D CH296567A (en) 1950-03-24 1950-03-24 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH296567A (en)

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