AT276366B - Process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid in crystal form - Google Patents
Process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid in crystal formInfo
- Publication number
- AT276366B AT276366B AT419368A AT419368A AT276366B AT 276366 B AT276366 B AT 276366B AT 419368 A AT419368 A AT 419368A AT 419368 A AT419368 A AT 419368A AT 276366 B AT276366 B AT 276366B
- Authority
- AT
- Austria
- Prior art keywords
- pyrrolidone
- carboxylic acid
- preparation
- arginine salt
- crystal form
- Prior art date
Links
- ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 239000013078 crystal Substances 0.000 title description 2
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000001483 arginine derivatives Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung des neuen Argininsalzes der 2-Pyrrolidon-S-carbonsäure in Kristallform
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung des neuen Argininsalzes des 2-Pyrro- lidon-5-carbonsäure, der Formel
EMI1.1
EMI1.2
<Desc/Clms Page number 2>
des Argininsalzes der 2-Pyrrolidon-5-carbonsäure in Methylalkohol, welcher 350 ml wasserfreies Aceton beigesetzt wird, was einen Niederschlag von 3, 75 g des rohen Argininsalzes der 2-Pyrrolidon-5- -carbonsäure hervorruft.
Der Niederschlag wird mittels einer Glassinterplatte (mittlerer Porendurchmesser 40 bis 90/. 1) abfiltriert und das erhaltene Salz im Vakuum über wasserfreiem Kieselsäuregel getrocknet, anschliessend aus 99, öligen Methanol umkristallisiert, wobei pro Gramm Produkt 1 ml Methanol verwendet wird, und zuletzt nochmals im Vakuum über wasserfreiem Kieselsäuregel getrocknet.
Die umkristallisierte Endverbindung schmilzt bei 144 bis 1450C und weist bei der Elementaranalyse in Übereinstimmung mit der obigen Formel einen Stickstoff-Titer von 22, 50/0 (theoretisch 23, 09%) auf.
PATENTANSPRÜCHE :
1. Verfahren zur Herstellung des neuen Argininsalzes der 2-Pyrrolidon-5-carbonsäure, der Formel
EMI2.1
EMI2.2
ninbase und 2-Pyrrolidon-5-carbonsäure in 99,9%igem Methanol bei 700C in Lösung miteinander umsetzt, hierauf durch Zusatz von wasserfreiem Aceton rohes (I) ausfällt, dieses abfiltriert, trocknet, das getrocknete Produkt aus 99, 91olgem Methanol umkristallisiert und sodann nochmals trocknet.
<Desc / Clms Page number 1>
Process for the preparation of the new arginine salt of 2-pyrrolidone-S-carboxylic acid in crystal form
The invention relates to a process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid, of the formula
EMI1.1
EMI1.2
<Desc / Clms Page number 2>
of the arginine salt of 2-pyrrolidone-5-carboxylic acid in methyl alcohol, which is added to 350 ml of anhydrous acetone, which causes a precipitate of 3.75 g of the crude arginine salt of 2-pyrrolidone-5-carboxylic acid.
The precipitate is filtered off using a sintered glass plate (mean pore diameter 40 to 90/1) and the salt obtained is dried in vacuo over anhydrous silica gel, then recrystallized from 99 oily methanol, 1 ml of methanol being used per gram of product, and finally again in Vacuum dried over anhydrous silica gel.
The recrystallized end compound melts at 144 to 1450 ° C. and, in the elemental analysis in accordance with the above formula, has a nitrogen titer of 22.50/0 (theoretical 23.09%).
PATENT CLAIMS:
1. Process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid, of the formula
EMI2.1
EMI2.2
ninbase and 2-pyrrolidone-5-carboxylic acid in 99.9% methanol at 70 ° C. in solution, then crude (I) is precipitated by adding anhydrous acetone, this is filtered off, dried, the dried product is recrystallized from 99.91 molgem methanol and then dries again.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT419368A AT276366B (en) | 1968-04-30 | 1968-04-30 | Process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid in crystal form |
| ES366634A ES366634A1 (en) | 1968-04-30 | 1969-04-30 | Procedure for the preparation of pyrrolidoncarboxylate of arginine. (Machine-translation by Google Translate, not legally binding) |
| BR20981369A BR6909813D0 (en) | 1968-04-30 | 1969-04-30 | A CHEMICAL PROCESS FOR THE PREPARATION OF ARGININE PIRROLIDOUCARBOXYLATE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT419368A AT276366B (en) | 1968-04-30 | 1968-04-30 | Process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid in crystal form |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT276366B true AT276366B (en) | 1969-11-25 |
Family
ID=3560883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT419368A AT276366B (en) | 1968-04-30 | 1968-04-30 | Process for the preparation of the new arginine salt of 2-pyrrolidone-5-carboxylic acid in crystal form |
Country Status (3)
| Country | Link |
|---|---|
| AT (1) | AT276366B (en) |
| BR (1) | BR6909813D0 (en) |
| ES (1) | ES366634A1 (en) |
-
1968
- 1968-04-30 AT AT419368A patent/AT276366B/en active
-
1969
- 1969-04-30 ES ES366634A patent/ES366634A1/en not_active Expired
- 1969-04-30 BR BR20981369A patent/BR6909813D0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6909813D0 (en) | 1973-01-02 |
| ES366634A1 (en) | 1971-03-16 |
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