CH302068A - 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
- CH302068A CH302068A CH302068DA CH302068A CH 302068 A CH302068 A CH 302068A CH 302068D A CH302068D A CH 302068DA CH 302068 A CH302068 A CH 302068A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- ethyl ester
- acid ethyl
- preparation
- new
- 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
- 239000002253 acid Substances 0.000 claims description 5
- -1 p-benzyloxybenzoyl Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- ICEKEZSKMGHZNT-UHFFFAOYSA-N 4-phenylmethoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OCC1=CC=CC=C1 ICEKEZSKMGHZNT-UHFFFAOYSA-N 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 230000007717 exclusion Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 239000007787 solid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung eines neuen Aminoacetessigsäureäthylesterderivates. In Chemische Berichte , Band 82 (1949), Seiten 60-63, ist die Herstellung von a.cylier- ten a-Aminoacetessigestern beschrieben.
Es wurde nun gefunden, dass man zu einer neuen pharmazeutisch wertvollen Verbindung gelangt., wenn man Phenaeet.ylamino-aeetessig- säureätliylester in Gegenwart eines säurebin denden Mittels mit p-Bexizyloxybenzoylchlorid 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 I3ydroxylgruppen enthaltenden Lö sungsmitteln, wie z. B. Methylenchlorid, Te- traehlorkohl.enstoff, Chloroform, Äther usw., unter Ausschluss von Wasser arbeiten.
Der so erhaltene a-(p-Benzyloxybenzoyl)-a- phenaeetylamino-acetessigsäureäthylester der Formel
EMI0001.0018
schmilzt bei l.18-119 .
Die neue Verbindung soll als Chemo- therapeutikum oder als Zwischenprodukt für weitere Synthesen, z. B. von Aminosäuren oder Chemotherapeuticis, dienen.
<I>Beispiel:</I> Man löst 13,4 g a-Phenacetylamino-acet- essigsäureäthylester und 12,4 g p-Benzyloxy- benzoylchlorid in 80 em3 Methylenchlorid, gibt 5 g Caleiumhydroxyd (techn.) hinzu und schüttelt 15 Minuten lang, wobei sich die Lösung auf etwa 40 erwärmt.
Dann wird vom Niederschlag abgesaugt und das Methy- lenchlorid abdestilliert. Es hinterbleibt ein fester Rückstand, der nach dem Anteigen mit wenig Äther und Absaugen 17,5 g a-(p- Benzyloxybenzoyl) - a - phenacetylamino -aeet- essigsäureäthylester vom Fp. 118-119 lie fert.
Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. In Chemischeberichte, Volume 82 (1949), pages 60-63, the preparation of a.cylated a-aminoacetoacetic esters is described.
It has now been found that a new pharmaceutically valuable compound is obtained if one reacts Phenaeet.ylamino-aeetessig- sätliylester in the presence of an acid-binding agent with p-bexizyloxybenzoyl chloride.
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 solutions in no I3ydroxylgruppen containing solvents such. B. methylene chloride, Tetraehlorkohl.enstoff, chloroform, ether, etc., work with the exclusion of water.
The a- (p-benzyloxybenzoyl) -a-phenaeetylamino-acetic acid ethyl ester of the formula obtained in this way
EMI0001.0018
melts at l.18-119.
The new compound is said to be used as a chemotherapeutic agent or as an intermediate for further syntheses, e.g. B. of amino acids or chemotherapeuticis, serve.
<I> Example: </I> 13.4 g of a-phenacetylamino-acetic acid ethyl ester and 12.4 g of p-benzyloxy-benzoyl chloride are dissolved in 80 cubic meters of methylene chloride, 5 g of calcium hydroxide (technical) are added and the mixture is shaken for 15 minutes long, with the solution warming to about 40.
The precipitate is then filtered off with suction and the methylene chloride is distilled off. A solid residue remains which, after pasting with a little ether and suction, 17.5 g of a- (p-benzyloxybenzoyl) -a-phenacetylamino-aet- acetic acid ethyl ester of melting point 118-119.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE302068X | 1950-06-05 | ||
| CH295245T | 1951-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH302068A true CH302068A (en) | 1954-09-30 |
Family
ID=25733581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH302068D CH302068A (en) | 1950-06-05 | 1951-05-23 | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH302068A (en) |
-
1951
- 1951-05-23 CH CH302068D patent/CH302068A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE872041C (en) | Process for the production of water-soluble, asymmetrical condensation products | |
| DE2324993C3 (en) | 4'-DEHYDRO-OLEANDRIN, THE METHOD FOR MANUFACTURING THE SAME, AND A PHARMACEUTICAL PREPARATION CONTAINING THIS COMPOUND | |
| CH302070A (en) | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. | |
| CH302067A (en) | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. | |
| DE969245C (en) | Process for the production of new spasmolytically effective basic esters of ª ‡ -alkylated phenylacetic acids | |
| DE946145C (en) | Process for the preparation of alkyl or alkoxalkylaminobenzoic acid esters | |
| CH302069A (en) | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. | |
| CH302066A (en) | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. | |
| AT229291B (en) | Process for the preparation of 1,2-diaminocyclohexane or its salts or of 1,2-diaminocyclohexanetetraacetic acid | |
| AT222118B (en) | Process for the production of new dihydro- and tetrahydropyranylcarbinols or their O-acyl derivatives | |
| DE862010C (en) | Process for the preparation of new derivatives of nicotinic acid amide | |
| AT233745B (en) | Process for the production of reserpic acid esters and their salts | |
| DE1118197B (en) | Process for the production of 6-azasterines | |
| CH295245A (en) | Process for the preparation of a new aminoacetoacetic acid ethyl ester derivative. | |
| DE854045C (en) | Process for the preparation of Aryldialkylessigsaeureaminoalkylestern or their salts | |
| DE924030C (en) | Process for the production of new nicotinic acid amides, which are substituted on the amide nitrogen by basic radicals, as well as their quaternary and acid salts | |
| AT163167B (en) | Process for the preparation of basic esters and amides of 1-aryl-cycloalkyl-1-carboxylic acids | |
| CH263037A (en) | Process for the preparation of a new derivative of 2-oxy-5-aminobenzoic acid. | |
| DE1231692B (en) | Process for the preparation of glycyrrhetinic acid derivatives | |
| DE1134077B (en) | Process for the preparation of 3-chloro-10- (3'-dimethylaminopropyl) -phenthiazine | |
| DE1047767B (en) | Process for the preparation of therapeutically valuable phosphoric acid esters | |
| DE1294959B (en) | Process for the preparation of 2,3-bis- (1'-methyl-4'-oxo-cyclohexyl) -butene- (2) | |
| DE1670804A1 (en) | Process for the preparation of azetidin-2-one-4-carboxylic acids | |
| CH370064A (en) | Process for producing a double compound | |
| CH259121A (en) | Process for the preparation of a new piperidyl ketone. |