CH210729A - Process for the preparation of a monoester of the androstane series. - Google Patents
Process for the preparation of a monoester of the androstane series.Info
- Publication number
- CH210729A CH210729A CH210729DA CH210729A CH 210729 A CH210729 A CH 210729A CH 210729D A CH210729D A CH 210729DA CH 210729 A CH210729 A CH 210729A
- Authority
- CH
- Switzerland
- Prior art keywords
- diol
- androstane
- reaction
- preparation
- carried out
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001441 androstanes Chemical class 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 7
- XZASNRFIVYRQLU-GZJQNMKQSA-N C(CC)(=O)OC1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@H]2CC(CC[C@]12C)O Chemical compound C(CC)(=O)OC1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@H]2CC(CC[C@]12C)O XZASNRFIVYRQLU-GZJQNMKQSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FWAYUWSHYLKUEY-LFWYWRBCSA-N Androstane-3,17-diol dipropionate Chemical compound C([C@@H]1CC2)[C@H](OC(=O)CC)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC(=O)CC)[C@@]2(C)CC1 FWAYUWSHYLKUEY-LFWYWRBCSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- 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)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Monoesters der Androstanreihe. Es wurde gefunden, dass man zum Andro- stan-3,17-diol-17-propionat gelangen kann, wenn man Androstan-3,17-diol-dipropionat der Formel
EMI0001.0006
mit hydrolysierend wirkenden Mitteln be handelt.
Das so gewonnene Androstan-3,17-diol-17- propionat der Formel
EMI0001.0010
bildet farblose Kristalle. Das oben genannte Dipropionat wird zweckmässig nur mit der zur Abspaltung einer Propionylgruppe ausreichenden Menge des hydrolisierend wirkenden Mittels behandelt. Die Reaktion lässt sich z. B. in Methyl- oder Äthylalkohol, aber auch in höheren Al koholen; in Diogan, Aceton und dergl. durch führen.
Bei Verwendung von Alkoholen findet meist eine Umesterung statt, so dass beträcht lich weniger als die berechnete Menge Lauge verbraucht wird. Man ist deshalb nicht an die berechnete Menge Lauge gebunden, son dern kann auch mehr oder weniger verwenden. Dadurch, sowie durch die Konzentration der Lauge und die Temperatur lässt sich die Reaktionszeit günstig beeinflussen.
Die neue Verbindung dient als Zwischen produkt zur Herstellung therapeutisch ver wendbarer Stoffe oder kann selbst therapeu tische Verwendung finden.
Beispiel: 4,0 g Androstan-3,17-diol-dipropioriat, dessen beiden Hydroxylgruppen vermutlich trans-Konfiguration zukommt, werden mit 1000 cm3 Methylalkohol, dem man vorher 0,45 g Kaliumhydroxyd zugesetzt bat, 40 Stunden bei Zimmertemperatur stehen ge- lassen.
Nach dem Neutralisieren der Lösung wird diese im Vakuum stark eingeengt, das durch partielle Verseifung entstandene rohe Androstan-3,17-diol-17-propionat mit Wasser gefällt, in Äther aufgenommen und dann der Äther abgedampft. Den so erhaltenen rohen Monoester reinigt man unter Entfernung schwerlöslicher Bestandteile durch Umkristal- lisieren. Er bildet farblose Kristalle.
Process for the preparation of a monoester of the androstane series. It has been found that androstane-3,17-diol-17-propionate can be obtained if androstane-3,17-diol-dipropionate of the formula
EMI0001.0006
with hydrolyzing agents.
The androstane-3,17-diol-17-propionate of the formula obtained in this way
EMI0001.0010
forms colorless crystals. The above-mentioned dipropionate is expediently treated only with the amount of the hydrolyzing agent which is sufficient to split off a propionyl group. The reaction can be z. B. in methyl or ethyl alcohol, but also in higher Al alcohols; in Diogan, acetone and the like. Perform.
When alcohols are used, transesterification usually takes place, so that considerably less than the calculated amount of lye is used. You are therefore not bound to the calculated amount of lye, but can use more or less. This, as well as the concentration of the lye and the temperature, can favorably influence the reaction time.
The new compound serves as an intermediate product in the manufacture of therapeutically usable substances or can be used therapeutically itself.
Example: 4.0 g of androstane-3,17-diol-dipropioriate, whose two hydroxyl groups presumably have a trans configuration, are left to stand for 40 hours at room temperature with 1000 cm3 of methyl alcohol to which 0.45 g of potassium hydroxide has been added beforehand .
After the solution has been neutralized, it is strongly concentrated in vacuo, the crude androstane-3,17-diol-17-propionate formed by partial saponification is precipitated with water, taken up in ether and then the ether is evaporated off. The crude monoester obtained in this way is purified by recrystallization while removing sparingly soluble constituents. It forms colorless crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH210729T | 1935-06-18 | ||
| CH207719T | 1935-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210729A true CH210729A (en) | 1940-07-31 |
Family
ID=25724442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210729D CH210729A (en) | 1935-06-18 | 1935-06-18 | Process for the preparation of a monoester of the androstane series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210729A (en) |
-
1935
- 1935-06-18 CH CH210729D patent/CH210729A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH210729A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH210727A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH207719A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH210725A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH210724A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH210726A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH210728A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222950A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222952A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222946A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH210723A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222951A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222947A (en) | Process for the preparation of a monoester of the androstene series. | |
| CH222949A (en) | Process for the preparation of a monoester of the androstene series. | |
| DE1807585C3 (en) | 14,15beta-epoxy cardenolides, processes for their preparation and compositions containing them | |
| DE936592C (en) | Process for the production of a blood and urine sugar lowering preparation from trioxyflavone glucoside-containing parts of plants | |
| CH222955A (en) | Process for the preparation of a monoester of the androstane series. | |
| CH222954A (en) | Process for the preparation of a monoester of the androstane series. | |
| DE1643174C3 (en) | Process for the preparation of 16 acyl gitoxin | |
| CH222956A (en) | Process for the preparation of a monoester of the androstane series. | |
| DE956047C (en) | Process for the production of furano (4 ', 5': 6, 7) chromones | |
| CH222953A (en) | Process for the preparation of a monoester of the androstane series. | |
| DE843415C (en) | Process for the preparation of a guaiacol derivative | |
| CH222948A (en) | Process for the preparation of a monoester of the androstene series. | |
| DE1804392A1 (en) | 9-0-Kalamycin derivatives and process for their preparation |