DE1085145B - Process for the decomposition of racemic tropic acid into its optically active components - Google Patents
Process for the decomposition of racemic tropic acid into its optically active componentsInfo
- Publication number
- DE1085145B DE1085145B DEE17402A DEE0017402A DE1085145B DE 1085145 B DE1085145 B DE 1085145B DE E17402 A DEE17402 A DE E17402A DE E0017402 A DEE0017402 A DE E0017402A DE 1085145 B DE1085145 B DE 1085145B
- Authority
- DE
- Germany
- Prior art keywords
- tropic acid
- optically active
- active components
- decomposition
- acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- JACRWUWPXAESPB-UHFFFAOYSA-N tropic acid Chemical group OCC(C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-UHFFFAOYSA-N 0.000 title description 5
- 238000000354 decomposition reaction Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 11
- JACRWUWPXAESPB-QMMMGPOBSA-N Tropic acid Natural products OC[C@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-QMMMGPOBSA-N 0.000 claims description 9
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 claims description 5
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- JACRWUWPXAESPB-MRVPVSSYSA-N (S)-tropic acid Chemical compound OC[C@@H](C(O)=O)C1=CC=CC=C1 JACRWUWPXAESPB-MRVPVSSYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZGCHLAJIRWDGFE-UHFFFAOYSA-N 1-aminopropane-1,1-diol Chemical compound CCC(N)(O)O ZGCHLAJIRWDGFE-UHFFFAOYSA-N 0.000 description 1
- PIIQLZXRLGJEKE-LSDHHAIUSA-N 3-[(3r,4r)-3-ethenylpiperidin-4-yl]-1-quinolin-4-ylpropan-1-one Chemical compound C=C[C@H]1CNCC[C@H]1CCC(=O)C1=CC=NC2=CC=CC=C12 PIIQLZXRLGJEKE-LSDHHAIUSA-N 0.000 description 1
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 1
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 1
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 1
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 1
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- HOZOZZFCZRXYEK-GSWUYBTGSA-M butylscopolamine bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 HOZOZZFCZRXYEK-GSWUYBTGSA-M 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- -1 ethylhydrocupreidine Chemical compound 0.000 description 1
- 229950003871 ethylhydrocupreine Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- SUWZHLCNFQWNPE-LATRNWQMSA-N optochin Chemical compound C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 SUWZHLCNFQWNPE-LATRNWQMSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 1
- 229960002646 scopolamine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DEUTSCHESGERMAN
Die linksdrehende Modifikation der Tropasäure stellt einen wichtigen Bestandteil mehrerer Alkaloide und synthetischer Arzneimittel, wie des optisch aktiven Tropins (Hyosciamins), ferner des optisch aktiven Scopolamins (Hyoscins), dar. Das neuerdings in die Therapie eingeführte N-Butyl-scopolaminbromid enthält ebenfalls linksdrehende Tropasäure.The levorotatory modification of tropic acid is an important component of several alkaloids and synthetic drugs, such as the optically active tropine (hyosciamine), and also the optically active scopolamine (Hyoscins). The recently introduced into therapy also contains N-butyl-scopolamine bromide levorotatory tropic acid.
Es sind bereits mehrere Verfahren bekannt, um racemische Tropasäure unter Verwendung von- Chinin, Chinidin, Morphin, Äthylhydrocupreidin, Äthylhydrocuprein, Cinchotoxin und Chinotoxin in die optisch aktiven Antipoden zu zerlegen (vgl. »Berichte der Deutschen Chemischen Gesellschaft«, Bd. 22, S. 2591; »Journal of the Chemical Society«, London, Bd. 121, S. 2582 bis 2586, und Bd. 115, S. 838 bis 840).There are already several methods known to racemic Tropic acid using quinine, quinidine, morphine, ethylhydrocupreidine, ethylhydrocupreine, To break down cinchotoxin and quinotoxin into the optically active antipodes (cf. »reports of German Chemical Society ", Vol. 22, p. 2591; Journal of the Chemical Society, London, Vol. 121, Pp. 2582 to 2586, and vol. 115, pp. 838 to 840).
Bei diesen Verfahren wird stets zunächst das diastereomere Salz der rechtsdrehenden (H-)-Tropasäure ausgeschieden, die für die Herstellung von pharmazeutischen Produkten wertlos ist. Das wertvollere diastereomere Salz der linksdrehenden Modifikation verbleibt dagegen in ao der Mutterlauge, aus der es nur nach mehrmaliger umständlicher fraktionierter Kristallisation isoliert werden kann. Aus diesem Grunde sind die bekannten Verfahren für die Herstellung von (—)-Tropasäure in technischem Maßstab nicht geeignet.In this process, the diastereomeric salt of the dextrorotatory (H -) - tropic acid is always excreted first, which is worthless for the manufacture of pharmaceutical products. The more valuable diastereomeric salt the counter-clockwise modification, however, remains in ao of the mother liquor, from which it only becomes more complicated after several times fractional crystallization can be isolated. For this reason, the known methods not suitable for the production of (-) - tropic acid on an industrial scale.
Es wurde nun gefunden, daß die racemische Tropasäure über ihre stereomeren Salze mit optisch aktivem threol-(p-Nitrophenyl)-2-amino-l,3-propandiol sehr leicht in die optischen Antipoden zerlegt werden kann, wobei sich bei Anwendung von d(—)-threo-l-(p-Nitrophenyl)-2-amino-l,3-propandiol das stereomere Salz der (—)-Tropasäure in kristalliner Form leicht abscheidet und bei Anwendung von L(+)-l-threo-l-(p-Nitrophenyl)-2-amino-1,3-propandiol das stereomere Salz der (+)-Tropasäure sich in kristalliner Form isolieren läßt.It has now been found that the racemic tropic acid via its stereomeric salts with optically active threol- (p-nitrophenyl) -2-amino-1,3-propanediol can very easily be broken down into the optical antipodes, with the use of d (-) - threo-l- (p-nitrophenyl) -2-amino-1,3-propanediol the stereomeric salt of (-) - tropic acid easily separates in crystalline form and at Use of L (+) - l-threo-l- (p-nitrophenyl) -2-amino-1,3-propanediol the stereomeric salt of (+) - tropic acid can be isolated in crystalline form.
Aus den getrennten diastereomeren Salzen kann die optisch aktive Tropasäure in einfacher Weise, großer Reinheit und sehr guter Ausbeute in an sich bekannter Weise gewonnen werden.The optically active tropic acid can be obtained from the separated diastereomeric salts in a simple, large manner Purity and very good yield can be obtained in a manner known per se.
Verfahren zur ZerlegungProcedure for dismantling
von racemischer Tropasäureof racemic tropic acid
in ihre optisch aktiven Komponenteninto their optically active components
Anmelder:Applicant:
Egyesült Gyogyszer- es Tapszergyär,
BudapestEgyesält Gyogyszer- es Tapszergyär,
Budapest
Vertreter:Representative:
Dr. G. W. Lotterhos und Dr.-Ing. H. W. Lotterhos,
Patentanwälte, Frankfurt/M., Lichtensteinstr. 3Dr. GW Lotterhos and Dr.-Ing. HW Lotterhos,
Patent attorneys, Frankfurt / M., Lichtensteinstr. 3
Beanspruchte Priorität:
Ungarn vom 31. März 1958Claimed priority:
Hungary from March 31, 1958
Dr.-Chem. Gabor Fodor und Ggörgy Csepreghy,Dr.-Chem. Gabor Fodor and Ggörgy Csepreghy,
Budapest,
sind als Erfinder genannt wordenBudapest,
have been named as inventors
26,7 g racemische Tropasäure und 34 g d(—)-threol-(p-Nitrophenyl)-2-amino-l,3-propandiol werden in 275 ecm Wasser von 40 bis 50° C gelöst. Die Lösung wird filtriert und das Filtrat mit Kristallen des Aminoalkohols geimpft. Die Lösung läßt man nun bei einer Temperatur von etwa 20 bis 25° C über Nacht stehen. Nach ungefähr 10 bis 15 Stunden kristallisiert in schönen Kristallen das aus (—)-Tropasäure und d(—)-threo-l-(p-Nitrophenyl)-2-amino-l,3-propandiol gebildete diastereomere Salz aus. Es wird abfiltriert, zweimal mit 15 ecm Eiswasser gewaschen und getrocknet. Ausbeute 27 g (=90%); F. = 107° C.26.7 g of racemic tropic acid and 34 g of d (-) - threol- (p-nitrophenyl) -2-amino-1,3-propanediol are dissolved in 275 ecm of water at 40 to 50 ° C. The solution is filtered and the filtrate with crystals of the amino alcohol vaccinated. The solution is then left to stand at a temperature of about 20 to 25 ° C. overnight. After about 10 to 15 hours crystallizes from (-) - tropic acid and d (-) - threo-1- (p-nitrophenyl) -2-amino-1,3-propanediol in beautiful crystals formed diastereomeric salt. It is filtered off, washed twice with 15 ecm of ice water and dried. Yield 27 g (= 90%); F. = 107 ° C.
Zur Gewinnung von (—)-Tropasäure werden 27 g des erhaltenen Salzes in 25 ecm Wasser unter Erwärmen gelöst und bei etwa 80° C mit 15 ecm konz. wäßrigem Ammoniak versetzt. Beim Abkühlen der Lösung fällt die Aminopropandiolbase kristallin aus und wird abfiltriert. Die Lösung wird, falls nötig, mit Tierkohle entfärbt und die farblose Lösung mit Salzsäure angesäuert. Beim Abkühlen fällt die (—)-Tropasäure aus, die abfiltriert wird. Durch Einengen der Mutterlauge bei vermindertem Druck kann man noch weitere Mengen (—)-Tropasäure gewinnen. Die erhaltene (—)-Tropasäure wird mit 10 ecm Eiswasser gewaschen und getrocknet. Ausbeute: 10 g (-)-Tropasäure (=77%); F. = 128° C; [a]f = -72°.To obtain (-) - tropic acid, 27 g of the salt obtained are heated in 25 ecm of water dissolved and at about 80 ° C with 15 ecm conc. aqueous ammonia added. When the solution cools, it falls the aminopropanediol base crystallizes out and is filtered off. If necessary, the solution is decolorized with animal charcoal and acidified the colorless solution with hydrochloric acid. On cooling, the (-) - tropic acid precipitates and is filtered off will. Further amounts can be obtained by concentrating the mother liquor under reduced pressure (-) - gain tropic acid. The (-) - tropic acid obtained is washed with 10 ecm of ice water and dried. Yield: 10 g of (-) - tropic acid (= 77%); Mp = 128 ° C; [a] f = -72 °.
Man verfährt in der im Beispiel 1 beschriebenen Weise, mit dem Unterschied, daß man als Base L(+)-threol-(p-Nitrophenyl)-2-amino-l,3-propandiolverwendet.Man erhält das diastereomere Salz der (-f-)-Tropasäure und des l(+) -threoj-1 - (p-Nitrophenyl)-2-amino-l,3-propandiols. Ausbeute: 27 g; F. = 107° C. Die Spaltung zuThe procedure described in Example 1 is repeated, with the difference that L (+) - threol- (p-nitrophenyl) -2-amino-1,3-propanediol is used as the base receives the diastereomeric salt of (-f -) - tropic acid and des l (+) -threoj-1 - (p-nitrophenyl) -2-amino-1,3-propanediol. Yield: 27 g; F. = 107 ° C. The cleavage too
009 550/341009 550/341
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1085145X | 1958-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1085145B true DE1085145B (en) | 1960-07-14 |
Family
ID=11003145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEE17402A Pending DE1085145B (en) | 1958-03-31 | 1959-03-28 | Process for the decomposition of racemic tropic acid into its optically active components |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1085145B (en) |
-
1959
- 1959-03-28 DE DEE17402A patent/DE1085145B/en active Pending
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