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DE918748C - Process for the preparation of oxoacetylamines (17-acetyl-aminoketones) of the cyclopentanopolyhydrophenanthrene series - Google Patents

Process for the preparation of oxoacetylamines (17-acetyl-aminoketones) of the cyclopentanopolyhydrophenanthrene series

Info

Publication number
DE918748C
DE918748C DEF7472A DEF0007472A DE918748C DE 918748 C DE918748 C DE 918748C DE F7472 A DEF7472 A DE F7472A DE F0007472 A DEF0007472 A DE F0007472A DE 918748 C DE918748 C DE 918748C
Authority
DE
Germany
Prior art keywords
oxoacetylamines
preparation
aminoketones
acetyl
cyclopentanopolyhydrophenanthrene series
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEF7472A
Other languages
German (de)
Inventor
Dr Josef Schmidt-Thome
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst 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 Hoechst AG filed Critical Hoechst AG
Priority to DEF7472A priority Critical patent/DE918748C/en
Application granted granted Critical
Publication of DE918748C publication Critical patent/DE918748C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Description

Verfahren zur Herstellung von Oxoacetylaminen (1'7-Acetylaminoketonen) der Cyclopentanopolyhydrophenanthrenreihe In dem Patent 915 938 sind verschiedene Wege beschrieben, die zu 17-Acylaminoketonen (Oxoacylamine) der Cyclopentanopolyhydrophenanthrenreihe führen, und zwar acyliert man in bekannter Weise entsprechende gesättigte oder ungesättigte Oxoamine, oder man oxydiert in bekannter Weise gesättigte oder ungesättigte Oxyacylaminoverbindungen.A process for preparing Oxoacetylaminen (1'7-Acetylaminoketonen) of the Cyclopentanopolyhydrophenanthrenreihe In Patent 915,938 different ways are described which lead to 17-Acylaminoketonen (Oxoacylamine) of the Cyclopentanopolyhydrophenanthrenreihe, namely acylating in a known manner corresponding saturated or unsaturated Oxoamine, or saturated or unsaturated oxyacylamino compounds are oxidized in a known manner.

Es wurde nun ein weiterer Weg zu ihrer Herstellung gefunden. Man unterwirft 2o-Monoxime von gesättigten oder ungesättigten Polyketonen der Steroidreihe, insbesondere von 3, 2o-Diketonen, die außerdem noch Substituenten tragen können und die z. B. durch Dehydrierung von Oxy-ao-ketonoximen mit Metallalkoholaten und einem Keton in einem inerten Lösungsmittel zugänglich sind, der Beckmannschen Umlagerung, beispielsweise mit Phosphoroxychlorid und Pyridin. Man erhält z. B. aus Progesteron-(2o)-monoxim das 17-Acetylamino-44-androsten-on-(3). Die freie Ketogruppe wird hierbei nicht angegriffen. Beispiel 5oo mg Progesteron-(2o)-monoxim werden in 5 ccm Pyridin gelöst, unter Eiskühlung wird eine Lösung von 0,7 ccm Phosphoroxychlorid in 2 ccm Pyridin zugesetzt und die Mischung 3 Stunden bei o° aufbewahrt. Nach dem Eingießen in ein Gemisch von Eiswasser und Salzsäure wird das ausgeflockte Reaktionsprodukt abfiltriert, mit Wasser gewaschen und getrocknet. Man erhält 390 mg des rohen i7-Acetylamino-d4-androsten-on-(3) vom Schmelzpunkt 25o°. Beim UmkristaIlisieren aus Alkohol erhält man das reine Produkt vom Schmelzpunkt 26:a.°, das mit dem im Hauptpatent 915 93$ beschriebenen Produkt bei der Mischprobe keine Depression ergibt.Another way of making them has now been found. One subjects 2o-monoximes of saturated or unsaturated polyketones of the steroid series, in particular of 3, 2o-diketones, which can also carry substituents and the z. B. are accessible by dehydrogenation of oxy-ao-ketone oximes with metal alcoholates and a ketone in an inert solvent, the Beckmann rearrangement, for example with phosphorus oxychloride and pyridine. One obtains z. B. from progesterone (2o) monoxime 17-acetylamino-44-androsten-one- (3). The free keto group is not attacked here. EXAMPLE 500 mg of progesterone (2o) monoxime are dissolved in 5 cc of pyridine, a solution of 0.7 cc of phosphorus oxychloride in 2 cc of pyridine is added while cooling with ice, and the mixture is stored at 0 ° for 3 hours. After pouring into a mixture of ice water and hydrochloric acid, the flocculated reaction product is filtered off, washed with water and dried. 390 mg of the crude 17-acetylamino-d4-androsten-one- (3) with a melting point of 250 ° are obtained. When recrystallizing from alcohol, the pure product is obtained with a melting point of 26: a °, which, with the product described in the main patent 915 93 $, does not result in any depression in the mixed sample.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Oxoacetylaminen (i7-Acetylaminoketonen) der Cyclopentanopolyhydrophenanthrenreihe nach Patent 915 938, dadurch gekennzeichnet, daß man 2o-Monoxime von Polyketonen der Steroidreihe, insbesondere von 3, 2o-Di'ketonen, die gesättigt oder ungesättigt sein und außerdem noch Substituenten tragen können, der Umlagerung nach Beckmann in bekannter Weise unterwirft.PATENT CLAIM: Process for the preparation of oxoacetylamines (i7-acetylaminoketones) of the cyclopentanopolyhydrophenanthrene series according to patent 915 938, characterized in that 2o-monoximes of polyketones of the steroid series, in particular 3, 2o-di'ketones, which are saturated or unsaturated and also still Can carry substituents, subject to the Beckmann rearrangement in a known manner.
DEF7472A 1951-06-06 1951-11-03 Process for the preparation of oxoacetylamines (17-acetyl-aminoketones) of the cyclopentanopolyhydrophenanthrene series Expired DE918748C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF7472A DE918748C (en) 1951-06-06 1951-11-03 Process for the preparation of oxoacetylamines (17-acetyl-aminoketones) of the cyclopentanopolyhydrophenanthrene series

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE736407X 1951-06-06
DEF7472A DE918748C (en) 1951-06-06 1951-11-03 Process for the preparation of oxoacetylamines (17-acetyl-aminoketones) of the cyclopentanopolyhydrophenanthrene series

Publications (1)

Publication Number Publication Date
DE918748C true DE918748C (en) 1954-10-04

Family

ID=25947281

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF7472A Expired DE918748C (en) 1951-06-06 1951-11-03 Process for the preparation of oxoacetylamines (17-acetyl-aminoketones) of the cyclopentanopolyhydrophenanthrene series

Country Status (1)

Country Link
DE (1) DE918748C (en)

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