DE839940C - Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acids - Google Patents
Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acidsInfo
- Publication number
- DE839940C DE839940C DEK5437A DEK0005437A DE839940C DE 839940 C DE839940 C DE 839940C DE K5437 A DEK5437 A DE K5437A DE K0005437 A DEK0005437 A DE K0005437A DE 839940 C DE839940 C DE 839940C
- Authority
- DE
- Germany
- Prior art keywords
- methylmercapto
- choline
- acylaminobutyric
- acid
- salt
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims description 12
- 239000002253 acid Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 3
- 150000007513 acids Chemical class 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title description 2
- 229960001231 choline Drugs 0.000 claims description 9
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 9
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- -1 acyl methionine Chemical compound 0.000 description 5
- 229930182817 methionine Natural products 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von organischen Salzen von y-Methylmercapto-a-acylaminobuttersäuren Gegenstand des Patents 8oi 839 ist ein Verfahren zur Herstellung eines organischen Salzes der y-Methylmercapto-a-aminobuttersäure, welches darin besteht, daß man die Aminosäure als solche mit Cholin oder ein geeignetes Salz der Aminosäure mit mineralsaurem Cholin umsetzt.Process for the preparation of organic salts of γ-methylmercapto-α-acylaminobutyric acids The subject of the patent 8oi 839 is a method for producing an organic Salt of γ-methylmercapto-a-aminobutyric acid, which consists in the fact that the Amino acid as such with choline or a suitable salt of the amino acid with mineral acid Choline converts.
Es wurde nun weiterhin gefunden, daß man in gleicher Weise auch mit am Stickstoff acylierten y-hletlivlmercapto-a-aminobuttersäuren Salze des Cholins herstellen kann. Diese Salze haben vor den nicht acylierten Verbindungen den Vorteil, daß ihre wäßrigen Lösungen neutral reagieren, was z. B. bei Verwendung solcher wäßriger Lösungen für Injektionszwecke gegenüber den schwach basischen Methionincholinlösungen von wesentlichem Vorteil ist.It has now also been found that in the same way with y-hallivl-mercapto-a-aminobutyric acid salts of choline acylated on nitrogen can produce. These salts have the advantage over the non-acylated compounds, that their aqueous solutions react neutrally, which z. B. when using such aqueous Solutions for injection purposes compared to the weakly basic methionine choline solutions is of significant advantage.
Die neuen Salze werden dadurch hergestellt, daß man äquivalente Mengen Cholinbase und Acylmethionin, z. B. Acetylmethionin, in Gegenwart eines Lösungsmittels aufeinander einwirken läßt. Ferner werden die Salze auch dadurch erhalten, daß man ein Salz des betreffenden Acylmethionins, vorzugsweise ein Alkalisalz, mit der äquivalenten :Menge von mineralsaurem Cholin umsetzt, und zwar zweckmäßig in einem solchen Lösungsmittel, in welchem das bei der Umsetzung entstehende Alkalisalz unlöslich ist. An Stelle von einem Metallsalz des Acylmethionins kann man auch das Metallsalz bildende Stoffe, wie z. B. Acylmethionin und Alkalihydroxyd.oder -alkoholat, anwenden.The new salts are prepared by using equivalent amounts Choline base and acyl methionine, e.g. B. acetyl methionine, in the presence of a solvent can act on each other. Furthermore, the salts are also obtained by a salt of the acyl methionine in question, preferably an alkali salt, with the equivalent : Reacts amount of mineral acid choline, expediently in such a solvent, in which the Implementation of the resulting alkali salt insoluble is. The metal salt can also be used instead of a metal salt of acyl methionine forming substances, such as B. acyl methionine and alkali hydroxide or alcoholate use.
Beispiel In eine Lösung von 7i,i g Cholinchlorid in Zoo ccm absolutem Alkohol wird unter Rühren und Kühlen alkoholisches Natriumäthylat, erhalten aus 11,7 g Natrium in 25o ccm absolutem Alkohol, eingetragen. Das ausfallende Natriumchlorid wird abgetrennt und die alkoholische Lösung der Cholin-Base zu einer Lösung von 97,3 g Acetylmethionin in 8oo ccm. Wasser hinzugegeben, wobei eine Lösung von neutraler Reaktion erhalten wird. Nach dem Verdampfen des Wassers und Alkohols im Vakuum hinterbleibt das Cholinsalz des Acetylmethionins als syrupöse Masse.Example In a solution of 71.1 g of choline chloride in zoo ccm of absolute Alcohol is obtained from alcoholic sodium ethylate with stirring and cooling 11.7 g of sodium in 250 cc of absolute alcohol, entered. The precipitating sodium chloride is separated and the alcoholic solution of the choline base to a solution of 97.3 g of acetyl methionine in 8oo cc. Water added, a solution of neutral Reaction is obtained. After evaporation of the water and alcohol remains in vacuo the choline salt of acetylmethionine as a syrupy mass.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK5437A DE839940C (en) | 1950-07-08 | 1950-07-08 | Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK5437A DE839940C (en) | 1950-07-08 | 1950-07-08 | Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE839940C true DE839940C (en) | 1952-05-26 |
Family
ID=7210830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK5437A Expired DE839940C (en) | 1950-07-08 | 1950-07-08 | Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acids |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE839940C (en) |
-
1950
- 1950-07-08 DE DEK5437A patent/DE839940C/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE839940C (en) | Process for the preparation of organic salts of ª † -Methylmercapto-ª ‡ -acylaminobutyric acids | |
| DE930687C (en) | Process for the production of sulfonates | |
| DE738499C (en) | Process for the preparation of addition compounds of hexamethylenetetramine | |
| DE411956C (en) | Process for the production of soluble acidic calcium or calcium-magnesium salts of inositol phosphoric acid | |
| DE644194C (en) | Process for the preparation of compounds containing arsenic and sulfhydryl groups, which are readily soluble in water | |
| DE548813C (en) | Process for the production of diacetone alcohol | |
| DE965407C (en) | Process for the production of monomeric organic sulfur compounds | |
| DE699556C (en) | propylamine decoctions | |
| DE665793C (en) | Process for the preparation of ª ‰ - (p-Oxyphenyl) -isopropylmethylamine | |
| DE738908C (en) | Manufacture of protein substances | |
| DE920077C (en) | Process for the preparation of derivatives of p-aminosalicylic acid | |
| DE695317C (en) | Process for obtaining the adenosine from the corresponding picrate | |
| DE631678C (en) | Process for the preparation of derivatives of higher alcohols | |
| DE676050C (en) | Process for the preparation of 3-oxy-4-carbaminobenzene-1-arsic acid | |
| DE916645C (en) | Process for the preparation of a salt of phenolphthalein diphosphoric acid ester | |
| DE672372C (en) | Process for the preparation of ª ‰ - (p-Oxyphenyl) -isopropylmethylamine | |
| AT224267B (en) | Process for the production of new penicillin salts | |
| DE444064C (en) | Process for the preparation of water-soluble double compounds of digitoglycotannoids, the totality of digitalis glycosides in their natural form | |
| DE1593807C (en) | alpha ascine methyl or ethy (ester, as well as a process for their production | |
| DE1024948B (en) | Process for the preparation of 2-amino-2-deoxy-aldohexoses and their salts | |
| CH216822A (en) | Process for the production of a preparation from the blood sugar lowering hormone of the pancreas. | |
| DE1059911B (en) | Process for the preparation of the chemotherapeutically active N-n-propyl-ª ‡, ª ‰ -dimethylsuccinimide | |
| DE1945254A1 (en) | Streptomycin acylembonates as depot cpds | |
| DE1051103B (en) | Process for the production of an alkali, alkaline earth and halogen-free salt substitute | |
| DE1593807B1 (en) | alpha-AEscine methyl or ethyl ester and a process for their preparation |