CH309462A - Process for the preparation of a new ester. - Google Patents
Process for the preparation of a new ester.Info
- Publication number
- CH309462A CH309462A CH309462DA CH309462A CH 309462 A CH309462 A CH 309462A CH 309462D A CH309462D A CH 309462DA CH 309462 A CH309462 A CH 309462A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- preparation
- diketo
- new ester
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 5
- WHBHBVVOGNECLV-OBQKJFGGSA-N 11-deoxycortisol Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 WHBHBVVOGNECLV-OBQKJFGGSA-N 0.000 claims description 3
- WHBHBVVOGNECLV-UHFFFAOYSA-N 11-deoxy-17-hydroxy-corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 WHBHBVVOGNECLV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- 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)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Verfahren zur Herstellung eines neuen Esters. Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung des 21-Furan-2'- earbonsäureesters von Reichsteins Substanz S (d4-3,20-Diketo-17a,21-dioxy -pregnen) .
Der neue Ester wird erhalten, wenn man ein d4-3,20-Diketo-17a-oxy-pregnen der For mel
EMI0001.0010
mit einer Verbindung der Formel
EMI0001.0011
umsetzt., wobei X und Y bei der Reaktion sich mit Ausnahme eines in einem von ihnen ent haltenen Sauerstoffatoms abspaltende Reste bedeuten. Das Verfahrensprodukt, das 21- Furoat von Reiehsteins Substanz S ([d4-3,20- Diketo-17a-oxy-21-furoyl-(2')-oxy-pregnen] vom F. = 223-223,5 , ist neu. Es soll als Heilmittel verwendet werden.
Im Ausgangsstoff der oben angegebenen Formel kann X zum Beispiel eine Oxygruppe sein, die bei der Umsetzung mit Furan-2-car- bonsäure oder einem reaktionsfähigen Derivat davon, wie einem Halogenid, einem Ester oder dem Anhydrid, in An- oder Abwesenheit eines Kondensationsmittels die Furoyl - (2) - oxy- gruppe ergibt. Ferner kann der genannte Substituent in 21-Stellung eine veresterte Oxygruppe, z.
B. ein Halogenatom, darstellen, das bei der Behandlung mit Furan-2-carbon- säur e oder einem Salz davon die Furoyl- (2) - oxygruppe liefert.
<I>Beispiel:</I> 1 Gewichtsteil d4-3,20-Diketo-17a,21-dioxy- pregnen wird in 10 Volumteilen wasserfreiem Pyridin gelöst und unter Kühlung mit einer Eis-Koehsalzmischung mit 2 Volumteilen Furan-2-carbonsäurechlorid versetzt. Das Re aktionsgemisch lässt man 16 Stunden bei -15 stehen. Dann gibt man unter Eiskühlung vor sichtig Eis und darauf Wasser zu und filtriert das ausgefallene Produkt. Der mit Wasser ge waschene Filterrückstand wird mit 30 Volum- teilen Aceton gekocht.
Die Lösung wird dar auf abgekühlt und kristallisieren gelassen. Nach Umlösen aus einem Gemisch von Chloro form und Alkohol schmilzt das so erhaltene d4-3, 20-Diketo-17a-oxy-21-f uroyl- (2') -oxy-pre- gnen der Formel
EMI0001.0054
bei 223-223,5 ; [a] D = -f-182 4 (c = 0,900 in Chloroform).
Process for the preparation of a new ester. The present invention relates to a process for the preparation of the 21-furan-2'-carboxylic acid ester of Reichstein's substance S (d4-3,20-diketo-17a, 21-dioxy-pregnene).
The new ester is obtained if a d4-3,20-diketo-17a-oxy-pregnen of the formula
EMI0001.0010
with a compound of the formula
EMI0001.0011
Reacts., where X and Y are radicals which split off in the reaction with the exception of one of them contained oxygen atom. The product of the process, the 21-furoate from Reiehstein's substance S ([d4-3.20-diketo-17a-oxy-21-furoyl- (2 ') - oxy-pregnen] from F. = 223-223.5, is new It is said to be used as a remedy.
In the starting material of the formula given above, X can be, for example, an oxy group, which in the reaction with furan-2-carboxylic acid or a reactive derivative thereof, such as a halide, an ester or the anhydride, in the presence or absence of a condensing agent Furoyl - (2) - oxy group gives. Furthermore, said substituent in the 21-position can be an esterified oxy group, e.g.
B. represent a halogen atom, which on treatment with furan-2-carboxylic acid or a salt thereof yields the furoyl (2) oxy group.
<I> Example: </I> 1 part by weight of d4-3,20-diketo-17a, 21-dioxypregnen is dissolved in 10 parts by volume of anhydrous pyridine, and 2 parts by volume of furan-2-carboxylic acid chloride are added while cooling with an ice-salt mixture . The reaction mixture is left to stand at -15 for 16 hours. Then ice and then water are carefully added while cooling with ice, and the precipitated product is filtered off. The filter residue washed with water is boiled with 30 parts by volume of acetone.
The solution is then cooled and allowed to crystallize. After dissolving from a mixture of chloroform and alcohol, the resulting d4-3, 20-diketo-17a-oxy-21-furoyl- (2 ') -oxy-pregnen of the formula melts
EMI0001.0054
at 223-223.5; [a] D = -f-182 4 (c = 0.900 in chloroform).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH305882T | 1951-10-18 | ||
| CH309462T | 1951-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH309462A true CH309462A (en) | 1955-08-31 |
Family
ID=25735012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309462D CH309462A (en) | 1951-10-18 | 1951-10-18 | Process for the preparation of a new ester. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH309462A (en) |
-
1951
- 1951-10-18 CH CH309462D patent/CH309462A/en unknown
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