AT203641B - Process for the introduction of residues of poorly reactive carboxylic acids - Google Patents

Process for the introduction of residues of poorly reactive carboxylic acids

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Publication number
AT203641B
AT203641B AT42857A AT42857A AT203641B AT 203641 B AT203641 B AT 203641B AT 42857 A AT42857 A AT 42857A AT 42857 A AT42857 A AT 42857A AT 203641 B AT203641 B AT 203641B
Authority
AT
Austria
Prior art keywords
introduction
carboxylic acids
residues
reactive carboxylic
poorly reactive
Prior art date
Application number
AT42857A
Other languages
German (de)
Original Assignee
Schering Ag
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 Schering Ag filed Critical Schering Ag
Application granted granted Critical
Publication of AT203641B publication Critical patent/AT203641B/en

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  • Steroid Compounds (AREA)

Description

  

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  Verfahren zur Einführung von Resten wenig reaktionsfähiger Carbonsäuren 
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 werden, wie in Beispiel 1 angegeben, umgesetzt und aufgearbeitet. 



   Ausbeute : 860 mg = 66,5 % d. Th. 17   &alpha;-Oxyprogesteroncapronat.   F. =   120 - 121 C.   



   Es ist identisch mit authentischem Material, das nach bekanntem Verfahren mit Capronsäureanhydrid   inGegenwartvonp-Toluolsulfosäure   dargestellt wurde. Das beweist, dass trotz der sehr energischen   Reak-   tionsbedingungen keine sterischen Umlagerungen im Bereich des   Cyc10pentanringes   eingetreten sind. 



   Beispiel 3 : Einer auf 800 C erhitzten Mischung aus 4 cm3Cyclopentylproplonsäure und 1 cm3   Trifluoressigsäureanhydrid   wird 1 g 17   a-Oxyprogesteron   zugesetzt ; es wird analog Beispiel 1 umgesetzt und aufgearbeitet. 
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  Process for the introduction of residues of poorly reactive carboxylic acids
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 are, as indicated in Example 1, implemented and worked up.



   Yield: 860 mg = 66.5% of theory. Th. 17α-oxyprogesterone caproate. F. = 120 - 121 C.



   It is identical to authentic material that was prepared using a known method with caproic anhydride in the presence of p-toluenesulfonic acid. This proves that, despite the very energetic reaction conditions, no steric rearrangements occurred in the area of the cyclopentane ring.



   Example 3: 1 g of 17α-oxyprogesterone is added to a mixture of 4 cm3 of cyclopentylproplonic acid and 1 cm3 of trifluoroacetic anhydride heated to 800 ° C .; it is implemented and worked up analogously to Example 1.
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Claims (1)

:PATENTANSPRUCH : Verfahren zur Einführung der Reste wenig reaktionsfähiger Carbonsäuren, wie des e-Cyclopentyl- propionylrestes in die 17 a-Oxygruppe solcher Steroide, die am Kohlenstoffatom 17 neben der Oxygruppe eine Acetylgruppe tragen, dadurch gekennzeichnet, dass man die genannten Säuren wasserfrei in Gegenwart von Trifluoressigsäureanhydrid bei etwas erhöhten Temperaturen, vorzugsweise bei 80-90 C, auf die genannten Steroide einwirken lässt. : PATENT CLAIM: Process for the introduction of the radicals of less reactive carboxylic acids, such as the e-cyclopentylpropionyl radical in the 17 a-oxy group of those steroids which carry an acetyl group on carbon atom 17 in addition to the oxy group, characterized in that the acids mentioned are anhydrous in the presence of trifluoroacetic anhydride slightly elevated temperatures, preferably at 80-90 C, can act on the steroids mentioned.
AT42857A 1956-03-22 1957-01-21 Process for the introduction of residues of poorly reactive carboxylic acids AT203641B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE203641X 1956-03-22

Publications (1)

Publication Number Publication Date
AT203641B true AT203641B (en) 1959-05-25

Family

ID=5777546

Family Applications (1)

Application Number Title Priority Date Filing Date
AT42857A AT203641B (en) 1956-03-22 1957-01-21 Process for the introduction of residues of poorly reactive carboxylic acids

Country Status (1)

Country Link
AT (1) AT203641B (en)

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