CH309463A - Process for the preparation of a new ester. - Google Patents

Process for the preparation of a new ester.

Info

Publication number
CH309463A
CH309463A CH309463DA CH309463A CH 309463 A CH309463 A CH 309463A CH 309463D A CH309463D A CH 309463DA CH 309463 A CH309463 A CH 309463A
Authority
CH
Switzerland
Prior art keywords
preparation
oxy
diketo
new ester
formula
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 CH309463A publication Critical patent/CH309463A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren     zur    Herstellung     eines    neuen Esters.         Die    vorliegende Erfindung betrifft     ein     Verfahren zur Herstellung des     21-Furan-2'-          carbonsäureesters    von     17a-Oxy-corticosteron          (44-3,20-Diketo-11ss,17a,        21-trioxy    -p r     egnen)    .  



  Der neue Ester     wird    erhalten, wenn man  ein     d4-3,20-Diketo-11ss,17a-dioxy-pregnen    der  Formel  
EMI0001.0013     
    mit einer Verbindung der Formel  
EMI0001.0014     
         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     21-          Furoat    des     1.7a-Oxy-corticosterons        [44-3,20-          Diketo        -11ss,17a    -     dioxy-        21-furoyl-    (2')     -oxy-pre-          ";nen]    vom F. = 238,5-241,5 , ist neu. Es soll  als Heilmittel verwendet werden.

      sein, die bei der Umsetzung mit     Furän-2-car-          bonsäure    oder einem reaktionsfähigen Derivat  davon, wie einem     Halogenid,    einem Ester oder  dem     Anhydrid,    in An- oder Abwesenheit eines  Kondensationsmittels die     Furoyl    - (2) -     oxy-          gruppe    ergibt. Ferner kann der genannte       Substituent    in     21-Stellung    eine veresterte       Oxygruppe,    z.

   B. ein Halogenatom, darstellen,  das bei der Behandlung mit     Furan-2-carbon-          säure    oder einem Salz davon die     Furoyl-(2)-          oxygruppe    liefert.    <I>Beispiel:</I>    Zu einer Lösung von 0,33 Gewichtsteilen       44-3,20-diketo-11,6,17a,21.-trioxy-pregnen    in  5     Volumteilen        Pyridin    werden unter     Küh-          hing    mit einer     Eis-Kochsalzmischung    0,5     Vo-          lumteile        Furan-2-carbonsäurechlorid    gegeben.

    Nach 5/4 Stunden giesst man auf Eis,     fil-          triert    und wäscht mit Wasser, Methanol     und     Äther. Nach zweimaligem     Umkristallisieren     des so erhaltenen Rohproduktes aus einem  Gemisch von     Aceton    und Methanol erhält  man 0,22 Gewichtsteile des     d4-3,20-diketo-          11ss,17a-dioxy-21-furoyl-(2')-oxy-pregnens    vom  F. = 238,5-241,5 .



  Process for the preparation of a new ester. The present invention relates to a process for the preparation of the 21-furan-2'-carboxylic acid ester of 17a-oxycorticosterone (44-3,20-diketo-11ss, 17a, 21-trioxy-p regen).



  The new ester is obtained if a d4-3,20-diketo-11ss, 17a-dioxy-pregnen of the formula
EMI0001.0013
    with a compound of the formula
EMI0001.0014
         converts, where X and Y are radicals which split off in the reaction with the exception of one of them contained oxygen atom.

   The process product, the 21-furoate of 1.7a-oxy-corticosterone [44-3,20-diketo -11ss, 17a-dioxy- 21-furoyl- (2 ') -oxy-pre- "; nen] from F. = 238.5-241.5, is new, intended to be used as a remedy.

      be, which in the reaction with furan-2-carboxylic acid or a reactive derivative thereof, such as a halide, an ester or the anhydride, in the presence or absence of a condensing agent, gives the furoyl (2) oxy 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 furan-2-carboxylic acid or a salt thereof gives the furoyl (2) - oxy group. <I> Example: </I> To a solution of 0.33 parts by weight of 44-3,20-diketo-11,6,17a, 21-trioxy-pregnen in 5 parts by volume of pyridine, while cooling with an ice cream Salt mixture given 0.5 parts by volume of furan-2-carboxylic acid chloride.

    After 5/4 hours the mixture is poured onto ice, filtered and washed with water, methanol and ether. After the crude product thus obtained has been recrystallized twice from a mixture of acetone and methanol, 0.22 parts by weight of the d4-3,20-diketo-11ss, 17a-dioxy-21-furoyl- (2 ') -oxy-pregnens from F. = 238.5-241.5.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Esters, dadurch gekennzeichnet, dass man ein d4-3,20-Diketo-llss,17a-dioxy-pregnen der For mel Im Ausgangsstoff der oben angegebenen Formel kann X zum Beispiel eine Oxygruppe EMI0002.0001 io mit einer Verbindung der Formel umsetzt, wobei X und V bei der Reaktion sich mit Ausnahme eines in. einem von ihnen ent haltenen Sauerstoffatoms abspaltende Reste bedeuten. Claim: Process for the preparation of a new ester, characterized in that a d4-3,20-diketo-llss, 17a-dioxy-pregnen of the formula In the starting material of the formula given above, X can be, for example, an oxy group EMI0002.0001 io is reacted with a compound of the formula where X and V are radicals which are split off in the reaction, with the exception of an oxygen atom contained in one of them. Das Verfahrensprodukt, das 21- Furoat des 17a-Oxy-eortieosterons [44-3,20- Diketo-11,B,17a-dioxy -21-furoyl-(2')-oxy-pre- gnen, schmilzt bei 238,5-241,5 . EMI0002.0011 The product of the process, the 21-furoate of 17a-oxy-eortieosterone [44-3,20-diketo-11, B, 17a-dioxy -21-furoyl- (2 ') -oxy-pregnen, melts at 238.5 -241.5. EMI0002.0011
CH309463D 1951-10-18 1951-10-18 Process for the preparation of a new ester. CH309463A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH305882T 1951-10-18
CH309463T 1951-10-18

Publications (1)

Publication Number Publication Date
CH309463A true CH309463A (en) 1955-08-31

Family

ID=25735013

Family Applications (1)

Application Number Title Priority Date Filing Date
CH309463D CH309463A (en) 1951-10-18 1951-10-18 Process for the preparation of a new ester.

Country Status (1)

Country Link
CH (1) CH309463A (en)

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