CH227706A - Process for the preparation of d (+) - a, y-dioxy-B, B-dimethyl-butyric acid- (3'-oxy-propyl-) amide. - Google Patents
Process for the preparation of d (+) - a, y-dioxy-B, B-dimethyl-butyric acid- (3'-oxy-propyl-) amide.Info
- Publication number
- CH227706A CH227706A CH227706DA CH227706A CH 227706 A CH227706 A CH 227706A CH 227706D A CH227706D A CH 227706DA CH 227706 A CH227706 A CH 227706A
- Authority
- CH
- Switzerland
- Prior art keywords
- oxy
- dimethyl
- dioxy
- amide
- sep
- Prior art date
Links
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
- C07C233/16—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 singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Darstellung von d(+)-a, r-Dioay-ss, f-dimethyl-uuttersäure- (3'-ogy-propyl-)amid. Für die Herstellung der Pantothensäure und ihrer Homologen wird d,(-)-a-Oxy-ss,ss- dimethyl-y-butyrolactan mit ss-Alanin, seinen Salzen oder Estern, oder mit entsprechenden andern Aminoe:arbonsäuren umgesetzt (siehe zum Beispiel Science, 91 [19403 S. 411;
Journ. of the Americ. Chem. <B>See,</B> 62 [1940] S. 1785; amerikanisches Patent Nr. 2234680; Helv. Chim. Acta, 23 [19401 S. 651; Journ. of the Americ. Chem. Soc., 62 [1940] S. 1628).
Es wurde nun gefunden, dass man zu neuen A.bkö:mmlingen der d(-)-a,y-Dioxy-ss,ss-di- methyl-buttersäure gelangt, wenn man Al- kanolamine auf sie einwirken lässt. Die Um setzung wird vorzugsweise in einem Lösungs mittel durchgeführt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von d(+)-a,y- Dioxy - ss,ss - dimethyl - buttersäure - (3' - oxy- propyl-)-amid, welches dadurch gekennzeich net ist, da.ss man d'(-)-a-Oxy-ss,ss-dimethyl- y-butyrolacto@n mit 3-Oxy-propylamin um setzt.
Das bisher unbekannte Verfahrenserzeug nis ist ein farbloses, zähflüssiges, leicht wasserl:öslich-es 0:1, welches unter 0,02 mm zwischen 118 und 120 siedet und für c = 3 in Watssser eine spezifische Drehung von a v = + 29,7 zeigt.
Die neue Verbindung vermag die Wir kungen der Pantothensäure auszuüben und soll als Arzneimittel Verwendung finden.
Beispiel: Man löst 130 Gewichtsteile d(-)-a-Oxy- ss,ss-.dimethyl-y-butyrolacton in 150 Vo:lum- teilen Methylalkohol. Zu der Lösung fügt man auf einmal 75 Gewichtsteile 3-Oxy-pro- pylamin und rührt gut .durch. Die Um setzung setzt unter Selbsterwärmung ein. Die Temperatur steigt langsam bis gegen 50 . Nach etwa 2 Stunden beginnt die Tem peratur wieder zu sinken.
Um vollständige Umsetzung herbeizuführen, lässt man noch 24 Stunden bei Zimmertemperatur stehen. Das ,gebildete d(+)-a,y-Dioxy-ss"B-dimethyl- buttersäure- (3'-,oxy-propyl-)amid wird im Vakuum vom Methylalkohol befreit. Es binterbleibt als farbloses, zähflüssiges, leicht wasserlösliches Öl.
Process for the preparation of d (+) - a, r-Dioay-ss, f-dimethyl-butyric acid- (3'-ogy-propyl-) amide. For the preparation of pantothenic acid and its homologues, d, (-) - a-oxy-ss, ss-dimethyl-y-butyrolactane is reacted with s-alanine, its salts or esters, or with other corresponding amino acids (see for example Science, 91 [19403 p. 411;
Journ. of the Americ. Chem. See, 62 [1940] p. 1785; American Patent No. 2234680; Helv. Chim. Acta, 23 [19401 p. 651; Journ. of the Americ. Chem. Soc., 62 [1940] p. 1628).
It has now been found that new types of d (-) - a, y-dioxy-ss, ss-dimethyl-butyric acid can be obtained if alkanolamines are allowed to act on them. The implementation is preferably carried out in a solvent.
The subject of the present patent is a process for the preparation of d (+) - a, y-dioxy - ss, ss - dimethyl - butyric acid - (3 '- oxy-propyl -) - amide, which is characterized by da.ss one d '(-) - a-oxy-ss, ss-dimethyl-y-butyrolacto @ n with 3-oxy-propylamine to implement.
The previously unknown process product is a colorless, viscous, slightly water-soluble 0: 1, which boils below 0.02 mm between 118 and 120 and shows a specific rotation of av = + 29.7 for c = 3 in Watssser .
The new compound is able to exert the effects of pantothenic acid and should be used as a medicinal product.
Example: 130 parts by weight of d (-) - a-oxy-ss, ss-.dimethyl-y-butyrolactone are dissolved in 150 parts by volume of methyl alcohol. 75 parts by weight of 3-oxypropylamine are added all at once to the solution and the mixture is stirred thoroughly. The implementation begins with self-heating. The temperature rises slowly to around 50. After about 2 hours, the temperature begins to drop again.
In order to bring about complete conversion, it is left to stand at room temperature for a further 24 hours. The d (+) - a, y-dioxy-ss "B-dimethylbutyric acid (3 '-, oxy-propyl) amide formed is freed from methyl alcohol in vacuo. It remains as a colorless, viscous, easily water-soluble oil .
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH227706T | 1943-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH227706A true CH227706A (en) | 1943-06-30 |
Family
ID=4455191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH227706D CH227706A (en) | 1943-09-06 | 1942-05-08 | Process for the preparation of d (+) - a, y-dioxy-B, B-dimethyl-butyric acid- (3'-oxy-propyl-) amide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH227706A (en) |
-
1942
- 1942-05-08 CH CH227706D patent/CH227706A/en unknown
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