CH295245A - Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. - Google Patents
Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative.Info
- Publication number
- CH295245A CH295245A CH295245DA CH295245A CH 295245 A CH295245 A CH 295245A CH 295245D A CH295245D A CH 295245DA CH 295245 A CH295245 A CH 295245A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl ester
- acid ethyl
- preparation
- new
- aminoacetoacetic
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- DFWADNXPAGGDKQ-UHFFFAOYSA-N ethyl 4-amino-3-oxobutanoate Chemical class CCOC(=O)CC(=O)CN DFWADNXPAGGDKQ-UHFFFAOYSA-N 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 230000000973 chemotherapeutic effect Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 tetrahalorcarbon Chemical compound 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Aminoacetessigsäureäthylesterderivates. In Chemische Berichte , Band 82 (1949), Seiten 60-63, ist die Herstellung von acylier- ten a-Aminoacetessigestern beschrieben.
Es wurde nun gefunden, dass man zu einer neuen pharmazeutisch wertvollen Verbindung gelangt, wenn man Phenaeetylamino-acet- essigsäureäthylester in Gegenwart eines säure bindenden Mittels mit p-Nitrobenzoylchlorid umsetzt.
Als säurebindende Mittel kommen vorzugs weise Alkalien oder Erdalkalien, insbesondere die Hydroxyde, in Betracht.
Man kann die Umsetzung in wässerigem Medium durchführen. Jedoch kann man auch in keine Hydroxylgruppen enthaltenden Lö sungsmitteln, wie z. B. Methylenchlorid, Te- traehlorkohlenstoff, Chloroform, Äther usw. unter Ausschluss von Wasser arbeiten.
Der so erhaltene a-(p-Nitrobenzoyl)-a- phenacetylamino-acetessigsäureäthylester der Formel
EMI0001.0017
schmilzt bei 147 C.
Die neue Verbindung soll als Chemothera- peutikum oder als Zwischenprodukt für wei tere Synthesen, z. B. von Aminosäuren oder Chemotherapeuticis, dienen. <I>Beispiel 1:</I> 26,3 g Phenaeetylamino-acetessigsäure- äthylester werden mit 100 em3 Wasser und einer Lösung von 18,5 g p-Nitrobenzoylchlorid in 50 cm3 Benzol vereinigt und sofort unter kräftigem Rühren 7,5 g Caleiumhydroxyd in Wasser hinzugefügt.
Die Temperatur steigt so fort auf etwa 40 bis -45 , und es scheidet sich bald ein weisser Niederschlag aus. Nach 1/2- stündigem Rühren wird abgesaugt, mit Was ser und etwas Äther gewaschen und an der Luft getrocknet.
Erhalten werden 27 g a-(p-Nitrobenzoyl)- a - phenacetylamino - acetessigsäureäthylester der Formel
EMI0001.0039
welcher nach dem Umkristallisieren aus Essig ester 1 : 6 einen F. P. von 147 steigt.
<I>Beispiel 2:</I> 26,3 g a-Phenacetylamino-acetessigsäure- äthylester werden zu 18,5 g p-Nitrobenzoyl- ehlorid in 50 em3 Benzol gegeben, 17 g Baryt- hydrat in 150 em3 Wasser zugefügt und 1/4 Stunde kräftig geschüttelt.
Es werden 28 g a-(p-Nitrobenzoyl)-a-phen- acetylamino-acetessigsäiireäthylester mit dem in Beispiel 1 angegebenen Schmelzpunkt er halten.
Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. Chemical reports, volume 82 (1949), pages 60-63, describe the preparation of acylated α-aminoacetoacetic esters.
It has now been found that a new pharmaceutically valuable compound is obtained if phenaeetylamino-acetic acid ethyl ester is reacted with p-nitrobenzoyl chloride in the presence of an acid-binding agent.
As acid-binding agents, preference is given to alkalis or alkaline earths, in particular the hydroxides.
The reaction can be carried out in an aqueous medium. However, you can also in no hydroxyl-containing solvents Lö such. B. methylene chloride, tetrahalorcarbon, chloroform, ether etc. work with the exclusion of water.
The a- (p-nitrobenzoyl) -aphenacetylamino-acetic acid ethyl ester of the formula obtained in this way
EMI0001.0017
melts at 147 C.
The new compound is intended as a chemotherapeutic agent or as an intermediate for further syntheses, eg. B. of amino acids or chemotherapeuticis, serve. <I> Example 1: </I> 26.3 g of phenaeetylamino-acetic acid ethyl ester are combined with 100 cubic meters of water and a solution of 18.5 g of p-nitrobenzoyl chloride in 50 cm3 of benzene, and 7.5 g of potassium hydroxide are immediately combined with vigorous stirring added in water.
The temperature rises immediately to about 40 to -45, and a white precipitate soon separates out. After stirring for 1/2 hour, the mixture is filtered off with suction, washed with water and a little ether and air-dried.
27 g of a- (p-nitrobenzoyl) - a - phenacetylamino - acetic acid ethyl ester of the formula are obtained
EMI0001.0039
which after recrystallization from ethyl acetate 1: 6 increases an F.P. of 147.
<I> Example 2: </I> 26.3 g of a-phenacetylamino-acetic acid ethyl ester are added to 18.5 g of p-nitrobenzoyl chloride in 50 cubic meters of benzene, 17 g of baryta hydrate in 150 cubic meters of water are added and 1 Shaken vigorously for 4 hours.
There are 28 g of a- (p-nitrobenzoyl) -a-phen-acetylamino-acetessigsäiireäthylester with the melting point given in Example 1 he keep.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE295245X | 1951-05-23 | ||
| CH295245T | 1951-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH295245A true CH295245A (en) | 1953-12-15 |
Family
ID=25733578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH295245D CH295245A (en) | 1951-05-23 | 1951-05-23 | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH295245A (en) |
-
1951
- 1951-05-23 CH CH295245D patent/CH295245A/en unknown
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