AT160274B - Process for the preparation of 17-aminoandrosten- (4) -one- (3). - Google Patents
Process for the preparation of 17-aminoandrosten- (4) -one- (3).Info
- Publication number
- AT160274B AT160274B AT160274DA AT160274B AT 160274 B AT160274 B AT 160274B AT 160274D A AT160274D A AT 160274DA AT 160274 B AT160274 B AT 160274B
- Authority
- AT
- Austria
- Prior art keywords
- aminoandrosten
- preparation
- acid
- group
- carbonyl group
- Prior art date
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- Steroid Compounds (AREA)
Description
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Verfahren zur Herstellung von 17-Aminoandrosten- (4)-on- (3).
Es wurde gefunden, dass man 17-Aminoandrosten-(4)-on-(3) in der Weise herstellen kann, indem man eine 3-Acyloxyätiocholen-(5)-säure (österr. Patentschrift Nr. 159222) auf dem Wege des Abbaus nach Curtius in das entsprechende 3-Aeyloxy-17-aminoandrosten-(5) überführt und nach Verseifen der Estergruppe die in 3-Stellung befindliche sekundäre Carbinolgruppe unter vorübergehendem Schutz der Doppelbindung durch Halogenanlagerung zur Carbonylgruppe oxydiert.
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gedampft und das als Rückstand erhaltene Säurechlorid [II] in wässrigem Aceton mit der doppelt theoretischen Menge Natriumazid umgesetzt. Das Säureazid III], das an der Luft unbeständig ist, wird sofort in trockenem Toluol zu dem entsprechenden Isocyanat # [IV] verkocht.
4 g des so erhaltenen Isocyanats werden in 100 cm3 Äther, 100 e Benzol mit 150 g 60%iger Schwefelsäure 30 Minuten verseift ; die Temperatur wird dabei zweckmässig zwischen 0 und Zimmertemperatur gehalten. Das erhaltene Aminsulfat [V] wird in 7'5%iger alkoholischer Lauge aufgenommen und 24 Stunden sich selbst überlassen. Danach wird in Wasser gegossen und das kolloide Gemisch ausgeäthert. Nach Trocknen der ätherischen Lösung kann das Amin mit Salzsäure gefällt werden.
Zersetzungspunkt des salzsauren Amins [Vll bei 3000.
2. 5 g des so erhaltenen Aminhydrochlorids werden in 80 cm3 Eisessig gelöst ; in diese Lösung werden liy Brom in 20 cm3 Eisessig eintropfen gelassen und nun 1'73 Chromsäureanhydrid in 20cem3 50% igem Eisessig bei 0 hinzugesetzt. Nach 24stündigem Stehen bei 15 werden 2#5 g Zink- staub zur Lösung hinzugefügt und diese weitere sechs Stunden sich selbst überlassen. Nach Zugabe von 15 cm3 Benzol, 10 cm3 Wasser und noch 1 g Zinkstaub wird die Mischung 30 Minuten unter Rückfluss gekocht, schliesslich in Wasser gegossen, das Gemisch neutralisiert und das erhaltene Oxoamin [IXJ mit Natriumcarbonatlösung in Freiheit gesetzt.
Die oben beschriebens Reaktion wird durch die nachstehende Formeltabelle veranschaulicht.
Die so erhältliche Verbindung soll als Zwischenprodukt für die Herstellung pharmazeutisch wirksamer Verbindungen dienen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
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Process for the preparation of 17-aminoandrosten- (4) -one- (3).
It has been found that 17-aminoandrosten- (4) -one- (3) can be prepared in such a way that a 3-acyloxyethiocholenic (5) acid (Austrian Patent No. 159222) is degraded according to Curtius into the corresponding 3-aeyloxy-17-aminoandrosten- (5) and after saponification of the ester group the secondary carbinol group in the 3-position is oxidized with temporary protection of the double bond by halogen addition to the carbonyl group.
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evaporated and the acid chloride [II] obtained as residue reacted in aqueous acetone with twice the theoretical amount of sodium azide. The acid azide III], which is unstable in air, is immediately boiled in dry toluene to form the corresponding isocyanate # [IV].
4 g of the isocyanate obtained in this way are saponified in 100 cm3 of ether, 100 e of benzene with 150 g of 60% sulfuric acid for 30 minutes; the temperature is expediently kept between 0 and room temperature. The amine sulfate [V] obtained is taken up in 7.5% strength alcoholic lye and left to stand for 24 hours. Then it is poured into water and the colloidal mixture is extracted with ether. After the ethereal solution has dried, the amine can be precipitated with hydrochloric acid.
Decomposition point of the hydrochloric acid amine [VII at 3000.
2. 5 g of the amine hydrochloride obtained in this way are dissolved in 80 cm3 of glacial acetic acid; li bromine in 20 cm 3 of glacial acetic acid are added dropwise to this solution and 1,73 chromic anhydride in 20 cm 3 of 50% glacial acetic acid is then added at 0. After standing at 15 for 24 hours, 2 # 5 g of zinc dust is added to the solution and the solution is left to stand for an additional six hours. After adding 15 cm3 of benzene, 10 cm3 of water and another 1 g of zinc dust, the mixture is refluxed for 30 minutes, then poured into water, the mixture is neutralized and the oxoamine [IXJ obtained is released with sodium carbonate solution.
The reaction described above is illustrated by the formula table below.
The compound obtainable in this way is intended to serve as an intermediate for the preparation of pharmaceutically active compounds.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE160274X | 1936-03-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
AT160274B true AT160274B (en) | 1941-03-25 |
Family
ID=5681067
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AT160274D AT160274B (en) | 1936-03-28 | Process for the preparation of 17-aminoandrosten- (4) -one- (3). |
Country Status (1)
Country | Link |
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AT (1) | AT160274B (en) |
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- AT AT160274D patent/AT160274B/en active
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