CH282601A - Process for the preparation of a peptide-like derivative of the lysergic acid series. - Google Patents
Process for the preparation of a peptide-like derivative of the lysergic acid series.Info
- Publication number
- CH282601A CH282601A CH282601DA CH282601A CH 282601 A CH282601 A CH 282601A CH 282601D A CH282601D A CH 282601DA CH 282601 A CH282601 A CH 282601A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- methyl ester
- peptide
- derivative
- tryptophan methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical class C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 title description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- NCIHPOHJJSIWSC-IINYFYTJSA-N (6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carbonyl azide Chemical compound C(=O)([C@@H]1CN(C)[C@@H]2CC3=CNC4=CC=CC(C2=C1)=C34)N=[N+]=[N-] NCIHPOHJJSIWSC-IINYFYTJSA-N 0.000 claims description 3
- KCUNTYMNJVXYKZ-JTQLQIEISA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 KCUNTYMNJVXYKZ-JTQLQIEISA-N 0.000 claims description 3
- 235000005811 Viola adunca Nutrition 0.000 claims description 2
- 240000009038 Viola odorata Species 0.000 claims description 2
- 235000013487 Viola odorata Nutrition 0.000 claims description 2
- 235000002254 Viola papilionacea Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- -1 isolysergic acid compound Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
Landscapes
- Peptides Or Proteins (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Darstellung eines peptidartigen Derivates der Lysergsäure-Reihe. Das vorliegende Patent betrifft ein Ver fahren zur Darstellung von d-Isolysergyl-d- tryptophan-methylester, welches dadurch ge kennzeichnet ist, dass man d-Isolysergsäure- azid mit L-Tryptophan-methylester konden siert.
<I>Beispiel:</I> Eine frisch hergestellte Lösung von 1,O <B>g</B> d-Isolysergsäure-azid in 120 em3 Äther wird mit einer ätherischen Lösung von 0,75 g l - Tryptophan - methylester (entsprechend 1 Äquivalent bezogen auf das eingesetzte Azid) vermischt und nach Zusatz von 1 g trockenem, feingepulvertem Kaliumkarbonat 4 Stunden beim Raumtemperatur geschüttelt.
Der Eindampfrückstand der filtrierten, hellgelben Lösung lässt sich chromatographisch zerlegen. Man zieht die Substanz in wenig abs. Chloroform gelöst. an einer Säule aus 300 g Aluminiumoxyd auf und entwickelt mit dem gleichen Lösungsmittel. Im UV-Licht zei gen sich zwei blauleuchtende Hauptzonen, von denen die rascher wandernde die Isolyserg- säureverbindung enthält.
Der d-Isolysergyl-l-tryptophan-methylester, der in Alkohol, Aceton und Chloroform spie- lend löslich, in Äther und Benzol nur mässig löslich ist, liess sich nicht kristallisieren.
Bruttoformel C28H2803N4 Ber. C 71,76 1-16,03 N 11,97 % Gef. 72,06 6,04 11,86 [alD = + 197 (c = 0,5 in Chloroform) Bei der Kellerschen Farbreaktion macht sieh der Tryptophan-Rest, der selbst eine röt liche Farbreaktion gibt, bemerkbar, so dass ein blauvioletter Farbton resultiert.
Process for the preparation of a peptide-like derivative of the lysergic acid series. The present patent relates to a process for the preparation of d-isolysergyl-d-tryptophan methyl ester, which is characterized in that d-isolysergic acid azide is condensed with L-tryptophan methyl ester.
<I> Example: </I> A freshly prepared solution of 1.0 <B> g </B> d-isolysergic acid azide in 120 em3 ether is mixed with an ethereal solution of 0.75 g of tryptophan methyl ester (corresponding to 1 equivalent based on the azide used) and, after adding 1 g of dry, finely powdered potassium carbonate, shaken for 4 hours at room temperature.
The residue from evaporation of the filtered, light yellow solution can be broken down by chromatography. One pulls the substance in little abs. Dissolved chloroform. on a column of 300 g of aluminum oxide and developed with the same solvent. In the UV light there are two main zones that glow blue, of which the more rapidly migrating contains the isolysergic acid compound.
The d-isolysergyl-l-tryptophan methyl ester, which is sparingly soluble in alcohol, acetone and chloroform and only sparingly soluble in ether and benzene, could not be crystallized.
Gross formula C28H2803N4 calc. C 71.76 1-16.03 N 11.97% Gef. 72.06 6.04 11.86 [alD = + 197 (c = 0.5 in chloroform) In Keller's color reaction, the tryptophan residue makes which itself gives a reddish color reaction, noticeable so that a blue-violet hue results.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH282601T | 1948-09-17 | ||
| CH269795T | 1948-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH282601A true CH282601A (en) | 1952-04-30 |
Family
ID=25731102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH282601D CH282601A (en) | 1948-09-17 | 1948-09-17 | Process for the preparation of a peptide-like derivative of the lysergic acid series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH282601A (en) |
-
1948
- 1948-09-17 CH CH282601D patent/CH282601A/en unknown
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