CH296568A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH296568A
CH296568A CH296568DA CH296568A CH 296568 A CH296568 A CH 296568A CH 296568D A CH296568D A CH 296568DA CH 296568 A CH296568 A CH 296568A
Authority
CH
Switzerland
Prior art keywords
preparation
new ester
formula
trimethyl
oxy
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 CH296568A publication Critical patent/CH296568A/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     Trimethylaee-          tats    von     Cortison.     



  Der neue Ester wird erhalten,     wenn    man  ein     d4-3,11,20-Triketo-17a-oxy        -pregnen    der  Formel  
EMI0001.0010     
    mit einer Verbindung der Formel         (C1-13)        #-C-CO-Y       umsetzt, wobei X und Y bei der Reaktion  sieh mit Ausnahme eines in einem von ihnen       entlialte=nei@        Satterst:offatonl,5    abspaltende Reste  bedeuten.

   Das Verfahrensprodukt, das     Tri-          methylaeetat    von     Cortison    (d     4-3,11,20-Tri-          keto-17a-oxy-27        -trimethylaeetoxy-pi egnen)     vom F. = 260 bis     262 ,    soll als Heilmittel ver  wendet werden.  



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

   B. ein Halogenatom, darstellen,  das bei der Behandlung mit     Trimethylessig-          sä.ure    oder einem Salz davon die     Trimethyl-          aeetoxygruppe    liefert.    <I>Beispiel:</I>    1 Gewichtsteil d     4-3,11,20-Triketo-17a,21-          dioxy-pregnen    wird in 10     Volumteilen        Pyri-          din    gelöst und unter starker Kühlung trop  fenweise mit 5     Gewiehtsteilen        Trimethyl-aee-          tylchlorid    versetzt. lach einigem Stehen in  der Kälte giesst man die Reaktionsmischung  vorsichtig in. Wasser.

   Das ausgefällte d 4-3,11,  20     -Tr        iketo        -17a    -     oxy        -21.-trimethyl-acetoxy-pre-          gnen    der Formel  
EMI0001.0050     
    wird nach     Umlösen    aus Aceton als feine Na  deln von F. 260 bis 262  C erhalten [a] D       =    +210  (c = 0,910 in Chloroform).



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



  The new ester is obtained if a d4-3,11,20-triketo-17a-oxy -pregnen of the formula
EMI0001.0010
    with a compound of the formula (C1-13) # -C-CO-Y, where X and Y in the reaction see with the exception of one in one of them entlialte = nei @ Satterst: offatonl, mean 5 splitting off radicals.

   The process product, the trimethyl acetate of cortisone (d 4-3,11,20-triketo-17a-oxy-27 -trimethylaeetoxy-pi egnen) from F. = 260 to 262, is to be used as a remedy.



  In the starting material of the formula given above, X can be, for example, an oxy group which, when reacted with trimethyl acetic acid or a reactive derivative thereof, such as a halide, an ester or anhydride, in the presence or absence of a condensing agent, forms the Trimethvlaeetoxv- results. 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 yields the trimethyl aeetoxy group. <I> Example: </I> 1 part by weight of d 4-3,11,20-triketo-17a, 21-dioxy-pregnen is dissolved in 10 parts by volume of pyridine and, with strong cooling, added dropwise with 5 parts by weight of trimethyl-aee- tyl chloride added. After standing in the cold for a while, the reaction mixture is carefully poured into water.

   The precipitated d 4-3,11, 20 -Tr iketo -17a-oxy -21.-trimethyl-acetoxy-pregen of the formula
EMI0001.0050
    is obtained after redissolving from acetone as fine needles from F. 260 to 262 C [a] D = +210 (c = 0.910 in chloroform).

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Esters, dadureh gekennzeiehnet, dass man ein so d 4-3,11,20-Triketo-17a-oxy-pregnen der For mel EMI0002.0002 mit einer Verbindung der Formel (CH3)@C-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 Tri- methy lacetat von Cortison, schmilzt bei 260 bis 262 C. PATENT CLAIM: Process for the production of a new ester, dadureh gekennzeiehnet that such a d 4-3,11,20-triketo-17a-oxy-pregnen the formula EMI0002.0002 with a compound of the formula (CH3) @ C-CO-Y, where X and Y are radicals which are split off in the reaction with the exception of one of them contained oxygen atom. The process product, the trimethyl acetate of cortisone, melts at 260 to 262 C.
CH296568D 1950-03-24 1950-03-24 Process for the preparation of a new ester. CH296568A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH296568T 1950-03-24
CH293297T 1950-03-24

Publications (1)

Publication Number Publication Date
CH296568A true CH296568A (en) 1954-02-15

Family

ID=25733341

Family Applications (1)

Application Number Title Priority Date Filing Date
CH296568D CH296568A (en) 1950-03-24 1950-03-24 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH296568A (en)

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