CH205436A - Process for the preparation of a new ester of estradiol. - Google Patents
Process for the preparation of a new ester of estradiol.Info
- Publication number
- CH205436A CH205436A CH205436DA CH205436A CH 205436 A CH205436 A CH 205436A CH 205436D A CH205436D A CH 205436DA CH 205436 A CH205436 A CH 205436A
- Authority
- CH
- Switzerland
- Prior art keywords
- estradiol
- agent
- preparation
- isobutyrylating
- iso
- Prior art date
Links
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 title claims description 8
- 229960005309 estradiol Drugs 0.000 title claims description 8
- 229930182833 estradiol Natural products 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 3
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 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)
Description
Verfahren zur Darstellung eines neuen Esters des Oestradiols. Es wurde gefunden, dass man zu einem neuen Ester des Östradiols gelangen kann, wenn man 1 Mol Ostradiol mit 2 Mol eines iso-Butyrylierungsmittels umsetzt.
Als iso-Butyrylierungsmittel verwendet man zum Beispiel iso-Buttersäure-anhydrid, -halogenide, -ester oder die Säure selbst. Zweckmässig wird die Reaktion in Gegen wart von Lösungsmitteln, wie z. B. tertiären Basen wie Pyridin, Chinolin oder auch aro matischen Kohlenwasserstoffen durchge führt.
Das so erhaltene -Östradiol-di-iso-butyrat bildet Kristalle vom F. 100,5 bis 101,5 . Es soll therapeutische Verwendung finden.
<I>Beispiel:</I> 1 Teil Östradiol wird in 5 Teilen Pyri- din und 4 Teilen iso-Buttersäureanhydrid einige Zeit auf 120 bis<B>125'</B> erhitzt. Nach dem Erkalten wird mit 2n Schwefelsäure an gesäuert und durch langsame Zugabe vor 140 Teilen Wasser das Östradiol-die-iso-buty- rat zur Kristallisation gebracht. Nach eini gem Stehen werden die Kristalle abfiltriert und mit Schwefelsäure, Wasser, gesättig ter Natriumkarbonatlösung und wiederum mit Wasser gewaschen.
Die Reinigung er folgt durch Umkristallisieren aus Methanol- Wasser. Schmelzpunkt 100,5 bis 101,5 .
Die Reaktion kann auch in Anwesenheit anderer tertiärer Basen, wie z. B. Dimethyl- anilin, Chinolin und dergl. oder auch ohne solche Basen durchgeführt werden.
Process for the preparation of a new ester of estradiol. It has been found that a new ester of estradiol can be obtained if 1 mole of estradiol is reacted with 2 moles of an isobutyrylating agent.
The isobutyrylating agent used is, for example, isobutyric anhydride, halides, esters or the acid itself. The reaction is expediently carried out in the presence of solvents such as. B. tertiary bases such as pyridine, quinoline or aromatic hydrocarbons Runaway leads.
The -estradiol-di-iso-butyrate thus obtained forms crystals with a melting point of 100.5 to 101.5. It should find therapeutic use.
<I> Example: </I> 1 part of estradiol in 5 parts of pyridine and 4 parts of isobutyric anhydride is heated to 120 to <B> 125 '</B> for a while. After cooling, the mixture is acidified with 2N sulfuric acid and the estradiol-die-isobutyrate is brought to crystallization by slowly adding 140 parts of water. After standing for some time, the crystals are filtered off and washed with sulfuric acid, water, saturated sodium carbonate solution and again with water.
The purification he follows by recrystallization from methanol-water. Melting point 100.5 to 101.5.
The reaction can also be carried out in the presence of other tertiary bases, such as e.g. B. dimethyl aniline, quinoline and the like. Or can be carried out without such bases.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH205436T | 1936-07-30 | ||
| CH201115T | 1936-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH205436A true CH205436A (en) | 1939-06-15 |
Family
ID=25723663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH205436D CH205436A (en) | 1936-07-30 | 1936-07-30 | Process for the preparation of a new ester of estradiol. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH205436A (en) |
-
1936
- 1936-07-30 CH CH205436D patent/CH205436A/en unknown
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