AT208518B - Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure - Google Patents

Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure

Info

Publication number
AT208518B
AT208518B AT20657A AT20657A AT208518B AT 208518 B AT208518 B AT 208518B AT 20657 A AT20657 A AT 20657A AT 20657 A AT20657 A AT 20657A AT 208518 B AT208518 B AT 208518B
Authority
AT
Austria
Prior art keywords
syringoyl
diesters
carboxy
preparation
reserpsäure
Prior art date
Application number
AT20657A
Other languages
German (de)
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Priority to AT20657A priority Critical patent/AT208518B/en
Application granted granted Critical
Publication of AT208518B publication Critical patent/AT208518B/en

Links

Description

       

   <Desc/Clms Page number 1> 
 



  Verfahren zur Herstellung von Diestern der   0-[ 0'- Carboxy -syringoylI -reserpsäure    
Gegenstand der vorliegenden Erfindung ist   die Herstellung vonDiesternderO- [ (y-carboxy-syringoyl]-   reserpsäure der allgemeinen Formel 
 EMI1.1 
 
 EMI1.2 
 

 <Desc/Clms Page number 2> 

 
CarboxylgruppeMethyl-O-[O'-carboxyäthyl-syringoyl]-reserpat, das nach dem Umkristallisieren aus Aceton bei 175-178  schmilzt. 



   Nimmt man an Stelle des verwendeten Methyl-O-syringoyl-reserpates eine äquivalente Menge Äthyl-O-syringoyl-reserpat und verfährt im übrigen wie oben beschrieben, so erhält man das   Äthyl-0-   [O'-carbäthoxy-syringoyl]-reserpat. 



   Alkyl-reserpate, wie Methyl-und Äthyl-reserpate, lassen sich nach den von Dorfmann et al. in   Helv. Chim. Acta   37,59-75 [1954] gegebenen Vorschriften gewinnen. Die entsprechenden Syringasäure ester lassen sich nach an sich bekannten Methoden herstellen. 



    PATENTANSPRÜCHE :    
1. Verfahren zur Herstellung von Diestem der O-[O'-Carboxy-syringoyl]-reserpsäure der allgemeinen Formel : 
 EMI2.1 
 und deren Salze, worin Res für den in der Reserpsäure an die freie Hydroxyl- und Carboxylgrupper gebundenen zweiwertigen organischen Rest und R für Alkylreste stehen, dadurch gekennzeichnet, dass man Alkyl-O-syringoyl-reserpate mit einem Halogenkohlensäureäthylester umsetzt, und, wenn erwünscht, von erhaltenen Verbindungen Salze herstellt oder erhaltene Salze in die freien Verbindungen überführt.



   <Desc / Clms Page number 1>
 



  Process for the preparation of diesters of 0- [0'-carboxy-syringoylI -reserpsäure
The present invention relates to the preparation of diesters of O- [(γ-carboxy-syringoyl] reserps acid of the general formula
 EMI1.1
 
 EMI1.2
 

 <Desc / Clms Page number 2>

 
Carboxyl group methyl-O- [O'-carboxyäthyl-syringoyl] -reserpat, which melts at 175-178 after recrystallization from acetone.



   If, instead of the methyl-O-syringoyl-reserpates used, an equivalent amount of ethyl-O-syringoyl-reserpate is used and the procedure is otherwise as described above, the ethyl-O- [O'-carbethoxy-syringoyl] -reserpate is obtained.



   Alkyl reserpate, such as methyl and ethyl reserpate, can be prepared according to the method described by Dorfmann et al. in Helv. Chim. Acta 37.59-75 [1954] given regulations. The corresponding syringic acid esters can be prepared by methods known per se.



    PATENT CLAIMS:
1. Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure of the general formula:
 EMI2.1
 and their salts, in which Res stands for the divalent organic radical bonded to the free hydroxyl and carboxyl groups in the reserp acid and R stands for alkyl radicals, characterized in that alkyl-O-syringoyl-reserpate is reacted with an ethyl halocarbonate, and, if desired, prepares salts of compounds obtained or converts the salts obtained into the free compounds.

Claims (1)

2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass manmitChlorkohlensäureäthylester um- setzt. 2. The method according to claim 1, characterized in that the reaction is carried out with ethyl chlorocarbonate.
AT20657A 1954-05-05 1954-05-05 Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure AT208518B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT20657A AT208518B (en) 1954-05-05 1954-05-05 Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
AT20657A AT208518B (en) 1954-05-05 1954-05-05 Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure

Publications (1)

Publication Number Publication Date
AT208518B true AT208518B (en) 1960-04-11

Family

ID=3669613

Family Applications (1)

Application Number Title Priority Date Filing Date
AT20657A AT208518B (en) 1954-05-05 1954-05-05 Process for the preparation of diesters of O- [O'-Carboxy-syringoyl] -reserpsäure

Country Status (1)

Country Link
AT (1) AT208518B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1169952B (en) * 1960-10-26 1964-05-14 Roussel Uclaf Process for the preparation of optically active or racemic 18ª ‰ - (3 ', 4', 5'-trimethoxy-benzoyloxy) -10, 17ª ‡ -dimethoxy-16ª ‰ -carboxy-methyloxycarbonyl-3ª ‰, 20ª ‡ -yohimbane

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1169952B (en) * 1960-10-26 1964-05-14 Roussel Uclaf Process for the preparation of optically active or racemic 18ª ‰ - (3 ', 4', 5'-trimethoxy-benzoyloxy) -10, 17ª ‡ -dimethoxy-16ª ‰ -carboxy-methyloxycarbonyl-3ª ‰, 20ª ‡ -yohimbane

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