CH240102A - Process for the preparation of a lactone of the cyclopentanopolyhydrophenanthrene series. - Google Patents
Process for the preparation of a lactone of the cyclopentanopolyhydrophenanthrene series.Info
- Publication number
- CH240102A CH240102A CH240102DA CH240102A CH 240102 A CH240102 A CH 240102A CH 240102D A CH240102D A CH 240102DA CH 240102 A CH240102 A CH 240102A
- Authority
- CH
- Switzerland
- Prior art keywords
- lactone
- allo
- ester
- preparation
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000002596 lactones Chemical class 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- QYIXCDOBOSTCEI-FBVYSKEZSA-N epidihydrocholesterin Chemical compound C([C@@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-FBVYSKEZSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines Lactons der Cyclopentanopolyhydrophenanthren-Reihe. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Lactons der Cyclopentanopolyhydrophenanthren - Reihe, welches dadurch gekennzeichnet ist, dass man ein 3,21-Diacyloxy-allopregnan-20-on, das konfigurativ dem epi-Cholestanol entspricht, mit einem Halogenessigsäureester kondensiert und auf das Reaktionsprodukt wasserabspal tende und verseifende Mittel einwirken lässt.
Die so erhaltene neue Verbindung, das d '0,'--3,21 - Dioxy-nor-allo-cholensäure-lacton, schmilzt bei 24ä-244 . Sie soll therapeu tische Verwendung finden oder als Zwischen produkt zur Herstellung therapeutisch ver wendbarer Verbindungen dienen.
<I>Beispiel:</I> 600 mg 3,21- Diacetoxy - allo - pregnan- 20-on vom F. 156 , das konfigurativ dem epi- Cholestanol entspricht (erhalten aus 3-Acet- oxy-allo-ätio-cholansäure-methylester durch Überführung in an sich bekannter Weise über das 17-Säurechlorid zum 3-Acetoxy-17- diazoketon sowie anschliessende Behandlung mit Eisessig),
werden in 5 cm@ absolutem Benzol gelöst und mit 300 mg Bromessig ester und 120 mg Zink in Reaktion gebracht. Man erwärmt 2 Stunden auf dem Wasser bade, zersetzt dann mit Eis und verdünnter Salzsäure und nimmt das Reaktionsprodukt in Äther auf. Die Ätherlösung wird mit Wasser und verdünnter Bicarbonatlösüng ausgewaschen, über wasserfreiem Natrium sulfat getrocknet und eingedampft.
Der Rückstand wird zwecks Wasserabspaltung mit Acetanhydrid gekocht, wobei das 4 2o,22-3- Acetoxy -21- oxy - nor - allo- cholensäur e-lacton vom F. 230 erhalten wird. Es lässt sich durch saure Verseifung in das 42@@ 2-3,21 Dioxy-nor-allo-cholensäure-lacton vom F. 243 bis 244 umwandeln.
Process for the preparation of a lactone of the cyclopentanopolyhydrophenanthrene series. The subject of the present patent is a process for the production of a lactone of the cyclopentanopolyhydrophenanthrene series, which is characterized in that a 3,21-diacyloxy-allopregnan-20-one, which corresponds configuratively to the epi-cholestanol, is condensed with a haloacetic acid ester and on the reaction product allows dehydrating and saponifying agents to act.
The new compound obtained in this way, the d '0,' - 3,21 - dioxy-nor-allo-cholenic acid-lactone, melts at 24-244. It should find therapeutic use or serve as an intermediate product for the preparation of therapeutically ver usable compounds.
<I> Example: </I> 600 mg 3.21-diacetoxy-allo-pregnan-20-one from F. 156, which corresponds configuratively to epi-cholestanol (obtained from 3-acetoxy-allo-etio-cholanic acid methyl ester by conversion in a manner known per se via the 17-acid chloride to 3-acetoxy-17-diazoketone and subsequent treatment with glacial acetic acid),
are dissolved in 5 cm @ absolute benzene and reacted with 300 mg of bromoacetic ester and 120 mg of zinc. It is heated for 2 hours, bathed in water, then decomposed with ice and dilute hydrochloric acid and the reaction product is taken up in ether. The ethereal solution is washed out with water and dilute bicarbonate solution, dried over anhydrous sodium sulfate and evaporated.
The residue is boiled with acetic anhydride for the purpose of splitting off water, the 4 2o, 22-3-acetoxy-21-oxy-nor-allo- cholenic acid e-lactone having a melting point of 230 being obtained. It can be converted into the 42 @@ 2-3,21 dioxy-nor-allo-cholenic acid-lactone from F. 243 to 244 by acidic saponification.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240102T | 1938-09-15 | ||
| CH234780T | 1938-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240102A true CH240102A (en) | 1945-11-30 |
Family
ID=25727939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240102D CH240102A (en) | 1938-09-15 | 1938-09-15 | Process for the preparation of a lactone of the cyclopentanopolyhydrophenanthrene series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240102A (en) |
-
1938
- 1938-09-15 CH CH240102D patent/CH240102A/en unknown
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