CH215561A - Process for preparing the 2,5-dioxyvaleryl-B-alanine ethyl ester. - Google Patents

Process for preparing the 2,5-dioxyvaleryl-B-alanine ethyl ester.

Info

Publication number
CH215561A
CH215561A CH215561DA CH215561A CH 215561 A CH215561 A CH 215561A CH 215561D A CH215561D A CH 215561DA CH 215561 A CH215561 A CH 215561A
Authority
CH
Switzerland
Prior art keywords
ethyl ester
dioxyvaleric
alanine ethyl
dioxyvaleryl
acid
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH215561A publication Critical patent/CH215561A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung des     2,6-Dioayvaleryl-p-alaniaäthylesters.       Nach dem bisher bekannt gewordenen  Verfahren zur Darstellung von     Dioxyvalerian-          säure-@-alaniden    gewinnt man diese Verbin  dungen, indem man eine     Dioxyvaleriansäure          acetyliert,    die     acetylierte        Dioxyvaleriansäure     in ihr Säurechlorid überführt und dieses mit  einem     ss-Alaninester    zur Umsetzung bringt  (Journal of     the        American        Chemical        Society     61     [1939]    S.

   1616).  



  Es wurde nun ein neuer vorteilhafter Weg  zur Herstellung von     Dioxyvaleriansäure-;3-          alanidestern    oder     -amiden    aufgefunden. Er  findungsgemäss gelangt man zu den genannten  Verbindungen, wenn man das     Lacton    einer       Dioxyvaleriansäure    mit einem     @-Alaninester     oder     -amid    zur Umsetzung bringt. Zweck  mässigerweise     führt    man     die    Umsetzung unter  Verwendung eines     Lösungsmittels    und bei  erhöhter     Temperatur    durch.

    
EMI0001.0025     
    Die erfindungsgemässe     Verwendung    eines       Dioxyvaleriansäurelactons    an Stelle eines       acetylierten    Säurechlorids bietet     wesentliche     Vorteile. Diese liegen beispielsweise darin,  dass das     Lacton    der     2,4-Dioxyvaleriansäure     spontan entsteht, wenn man die     Säure    aus       ihren        Salzen    in Freiheit zu setzen versucht.

    Man erspart also zwei Umsetzungen, nämlich  die     Acetylierung    der     Oxygruppen    der     Dioxy-          valeriansäure    und die     Überführung    der     acety-          lierten        Oxysäure    in das Säurechlorid.  



  Gegenstand des     vorliegenden    Patentes ist  ein     Verfahren    zur Darstellung des     2,5-Dioxy-          valeryl-p-alaninäthylesters,    welches dadurch       gekennzeichnet    ist, dass     2,5-Dioxyvalerian-          säurelacton    mit     @-Alaninäthylester    umgesetzt  wird. Dieser Vorgang lässt sich durch fol  gendes Formelbild     veranschaulichen:         Der     2,5-Dioxyvaleryl-i3-alaninäth.#-lester     bildet ein farbloses, in Wasser gut lösliches,  viskoses 01, welches bei 0,001 mm Druck  und einer     Badtemperatur    von<B>1301</B> destilliert.

    Es ist auch in den meisten organischen Lö  sungsmitteln leicht löslich und stellt ein  Zwischenprodukt für die Gewinnung von       Arzneimitteln    dar.         CH90H-CH9-CH4-C1l011-CO-NH-Ct14--CH@-COOC211,       durch Destillation im     3lolekularkolben    bei  einer Temperatur von 130   und einem     Druck     von 0,001 mm gereinigt.



  Process for the preparation of 2,6-dioayvaleryl-p-alaniaethylester. According to the previously known process for the preparation of dioxyvaleric acid - @ - alanides, these compounds are obtained by acetylating a dioxyvaleric acid, converting the acetylated dioxyvaleric acid into its acid chloride and reacting this with an β-alanine ester (Journal of the American Chemical Society 61 [1939] p.

   1616).



  A new, advantageous way of producing dioxyvaleric acid; 3-alanide esters or amides has now been found. According to the invention, the compounds mentioned are obtained if the lactone of a dioxyvaleric acid is reacted with a @ -alanine ester or amide. The reaction is expediently carried out using a solvent and at an elevated temperature.

    
EMI0001.0025
    The use according to the invention of a dioxyvaleric acid lactone instead of an acetylated acid chloride offers significant advantages. These are, for example, that the lactone of 2,4-dioxyvaleric acid is formed spontaneously if one tries to set the acid free from its salts.

    Two reactions are thus saved, namely the acetylation of the oxy groups of the dioxyvaleric acid and the conversion of the acetylated oxy acid into the acid chloride.



  The subject of the present patent is a process for the preparation of 2,5-dioxyvaleryl-p-alanine ethyl ester, which is characterized in that 2,5-dioxyvaleric acid lactone is reacted with @ -alanine ethyl ester. This process can be illustrated by the following formula: The 2,5-Dioxyvaleryl-i3-alaninäth. # - lester forms a colorless, well soluble in water, viscous oil, which at 0.001 mm pressure and a bath temperature of <B> 1301 < / B> distilled.

    It is also easily soluble in most organic solvents and is an intermediate product for the production of pharmaceuticals. CH90H-CH9-CH4-C1l011-CO-NH-Ct14 - CH @ -COOC211, by distillation in a 3lolecular flask at a temperature of 130 and a pressure of 0.001 mm.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung des 2,:5-Dioxy- valeryl-ss-alaninäthylesters, dadurch gekenn zeichnet, dass 2,5-Dioxyvaleriansäurelacton mit ss-Alaninäthylester umgesetzt wird. <I>Beispiel:</I> <B>11,6</B> Gewichtsteile 2,5-Dioxyvaleriansäure- lacton (dargestellt aus d-Ornithin und Na triumnitrit und gereinigt durch Destillation im Vakuum, Kpl s = 127-135 ) werden mit 10 Raumteilen absolutem Alkohol verdünnt und auf 70-8011 erwärmt. PATENT CLAIM: Process for the preparation of 2,: 5-dioxyvaleryl-ß-alanine ethyl ester, characterized in that 2,5-dioxyvaleric acid lactone is reacted with ß-alanine ethyl ester. <I> Example: </I> <B> 11.6 </B> parts by weight of 2,5-dioxyvaleric acid lactone (made from d-ornithine and sodium nitrite and purified by distillation in vacuo, Kpl s = 127-135) are diluted with 10 parts by volume of absolute alcohol and heated to 70-8011. Nun lässt rrin innert 30 Minuten 11,7 Gewichtsteile @- Alani.näthy lester zutropfen. Nach dem Ab destillieren des Alkohols wird der 2,5-Dioxy- valeryl-@3-alani.näthylester von der Formel Der 2,5-Dioxyv:ileryl-i3-alariinäthylester bildet ein farbloses, in -Wasser gut lösliches, viskoses 01, welches bei 0,001 mm Druck und einer Badtemperatur von 130 destilliert. Es ist auch in den meisten organischen Lö sungsmitteln leicht löslich und stellt ein Zwi schenprodukt für die Gewinnung von Arznei mitteln dar. Now rrin allows 11.7 parts by weight of Alani.näthy lester to drip in within 30 minutes. After distilling off the alcohol, the 2,5-Dioxy- valeryl-@3-alani.näthylester of the formula The 2,5-Dioxyv: ileryl-i3-alariinäthylester forms a colorless, well soluble in water, viscous 01, which distills at 0.001 mm pressure and a bath temperature of 130. It is also easily soluble in most organic solvents and is an intermediate product for the production of pharmaceuticals.
CH215561D 1939-08-07 1939-08-07 Process for preparing the 2,5-dioxyvaleryl-B-alanine ethyl ester. CH215561A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH213249T 1939-08-07
CH215561T 1939-08-07

Publications (1)

Publication Number Publication Date
CH215561A true CH215561A (en) 1941-06-30

Family

ID=25725390

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215561D CH215561A (en) 1939-08-07 1939-08-07 Process for preparing the 2,5-dioxyvaleryl-B-alanine ethyl ester.

Country Status (1)

Country Link
CH (1) CH215561A (en)

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