CH240099A - 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
- CH240099A CH240099A CH240099DA CH240099A CH 240099 A CH240099 A CH 240099A CH 240099D A CH240099D A CH 240099DA CH 240099 A CH240099 A CH 240099A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- lactone
- allo
- acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000002596 lactones Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol 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-QCYZZNICSA-N 0.000 claims description 3
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 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
- 239000000203 mixture Substances 0.000 claims description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 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 Laetons der Cyelopentanopolyhydrophenanthren-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-allo - pregnan - 20 - on, das konfigurativ dem Cholestanol entspricht, mit einem Halogenessigsäureester kondensiert, aus dem entstandenen Gemisch das 42 ,
22-3-Acyl- oxy-21- oxy- nor - allocholen -säure - lacton ab trennt und auf diese Verbindung verseifende Mittel einwirken lässt.
Die so erhaltene neue Verbindung, das 42 @22-3,21-Dioxy-nor-allo - cholensäure - lacton, schmilzt bei 248 - 250 . Sie soll therapeu tische Verwendung finden oder als Zwischen produkt zur Herstellung therapeutisch ver wendbarer Verbindungen dienen.
Beispiel: 600 mg 3,21-Diacetoxy-allo-pregnan-20-on vom F. 153 -154 , das konfigurativ dem Cholestanol entspricht, werden in 5 cm' ab solutem Benzol gelöst und mit 300 mg Brom essigester und 120 mg Zink in Reaktion ge- bracht. Man erwärmt 2 Stunden auf dem Wasserbade, zersetzt dann mit Eis und ver dünnter Salzsäure und nimmt das Reaktions produkt in Äther auf. Die Ätherlösung wird mit Wasser und verdünnter Bicarbonatlösung ausgewaschen, über wasserfreiem Natrium sulfat getrocknet und eingedampft.
Der Rück stand wird mit 6 g Aluminiumoxyd vermischt und in einem Sublimationsgefäss bei 0,01 mm Druck auf 180 erwärmt, bis auf dem ge kühlten Kondensationsgefäss sich kein Destil lat mehr niederschlägt. Das Destillat wird in benzolischer Lösung an Aluminiumoxyd ad sorbiert und durch fraktionierte Elution mit Benzol, Äther und Aceton in eine Anzahl von Fraktionen zerlegt. Die verschiedenen Fraktionen werden im Legaltest geprüft und diejenigen, die' eine positive Farbreaktion geben, von den übrigen getrennt.
Durch frak tionierte Kristallisation aus Essigester-Hexan können die einzelnen Anteile gereinigt werden.
-Aus den Fraktionen mit positivem Legal test gewinnt man in der Hauptsache das .410,11-3_Acetoxy-21-oxy-nor - allo-cholen-säure-
EMI0002.0001
lacton <SEP> vom <SEP> F. <SEP> 193 <SEP> -194 , <SEP> das <SEP> durch <SEP> saure
<tb> Verseifung <SEP> in <SEP> das <SEP> cj211>22-3,21-D1oS.'-llol'-allo cholensäure-lacton <SEP> vom <SEP> F. <SEP> 248-250 <SEP> umge wandelt <SEP> wird.
Process for the preparation of a laeton of the cyelopentanopolyhydrophenanthrene 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-allo-pregnan-20-one, which corresponds configuratively to cholestanol, is condensed with a haloacetic acid ester the resulting mixture the 42,
22-3-acyl-oxy-21-oxy- nor - allocholenic acid - lactone separates and lets saponifying agents act on this compound.
The new compound obtained in this way, the 42 @ 22-3,21-dioxy-nor-allo-cholenic acid-lactone, melts at 248-250. It should find therapeutic use or serve as an intermediate product for the preparation of therapeutically ver usable compounds.
Example: 600 mg of 3,21-diacetoxy-allo-pregnan-20-one from F. 153-154, which corresponds configuratively to cholestanol, are dissolved in 5 cm 'of absolute benzene and mixed with 300 mg of bromoacetic ester and 120 mg of zinc in Reaction brought. It is heated for 2 hours on the water bath, then decomposed with ice and dilute hydrochloric acid and the reaction product is taken up in ether. The ether solution is washed out with water and dilute bicarbonate solution, dried over anhydrous sodium sulfate and evaporated.
The residue is mixed with 6 g of aluminum oxide and heated to 180 in a sublimation vessel at 0.01 mm pressure until no more distillate is deposited on the cooled condensation vessel. The distillate is adsorbed on aluminum oxide in a benzene solution and broken down into a number of fractions by fractional elution with benzene, ether and acetone. The various fractions are checked in the legal test and those that give a positive color reaction are separated from the others.
The individual components can be purified by fractional crystallization from ethyl acetate-hexane.
From the fractions with a positive legal test, the main thing to be obtained is .410,11-3_Acetoxy-21-oxy-nor - allo-cholen-acid-
EMI0002.0001
lacton <SEP> from <SEP> F. <SEP> 193 <SEP> -194, <SEP> the <SEP> by <SEP> acid
<tb> Saponification <SEP> in <SEP> the <SEP> cj211> 22-3,21-D1oS .'- llol'-allo cholenic acid-lactone <SEP> from <SEP> F. <SEP> 248-250 < SEP> is converted to <SEP>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240099T | 1938-09-15 | ||
| CH234780T | 1938-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240099A true CH240099A (en) | 1945-11-30 |
Family
ID=25727936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240099D CH240099A (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) | CH240099A (en) |
-
1938
- 1938-09-15 CH CH240099D patent/CH240099A/en unknown
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