DE1518029B1 - Stereospecific process for the production of l (-) - 3,4-Dimethoxyphenyl-acetyl-carbinol - Google Patents
Stereospecific process for the production of l (-) - 3,4-Dimethoxyphenyl-acetyl-carbinolInfo
- Publication number
- DE1518029B1 DE1518029B1 DE19651518029 DE1518029A DE1518029B1 DE 1518029 B1 DE1518029 B1 DE 1518029B1 DE 19651518029 DE19651518029 DE 19651518029 DE 1518029 A DE1518029 A DE 1518029A DE 1518029 B1 DE1518029 B1 DE 1518029B1
- Authority
- DE
- Germany
- Prior art keywords
- carbinol
- dimethoxyphenyl
- acetyl
- production
- medium
- 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 12
- MFVNSYUPVMVNRT-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-1-hydroxypropan-2-one Chemical compound COC1=CC=C(C(O)C(C)=O)C=C1OC MFVNSYUPVMVNRT-UHFFFAOYSA-N 0.000 title claims description 8
- 230000000707 stereoselective effect Effects 0.000 title claims description 3
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 241000588915 Klebsiella aerogenes Species 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OEGPRYNGFWGMMV-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanol Chemical compound COC1=CC=C(CO)C=C1OC OEGPRYNGFWGMMV-UHFFFAOYSA-N 0.000 description 2
- WVZMZBVNKYYIQB-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-hydroxypropan-2-one Chemical compound COC1=CC=C(CC(=O)CO)C=C1OC WVZMZBVNKYYIQB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004810 partition chromatography Methods 0.000 description 2
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- MZQGUGAQJZCZOC-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-4-methyl-2-oxo-1,3-oxazolidine-4-carboxamide Chemical compound C(N)(=O)C1(NC(OC1C1=CC(=C(C=C1)OC)OC)=O)C MZQGUGAQJZCZOC-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- -1 aryl acetyl carbinols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D29/00—Filters with filtering elements stationary during filtration, e.g. pressure or suction filters, not covered by groups B01D24/00 - B01D27/00; Filtering elements therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von l(—)-3,4-Dimethoxyphenyl-acetyl-carbinol. Diese Verbindung ist neu. Sie dient als Ausgangsprodukt zur Herstellung von L-«-Methyl-3,4-dihydroxyphenylalanin, einem bekannten Mittel zur Behandlung von hohem Blutdruck.The invention relates to a process for the preparation of l (-) - 3,4-dimethoxyphenyl-acetyl-carbinol. These Connection is new. It serves as a starting product for Preparation of L - «- methyl-3,4-dihydroxyphenylalanine, a known agent for the treatment of high blood pressure.
Es ist aus der USA.-Patentschrift 1 962 476 bekannt, optisch aktive Aryl-acetylcarbinole, z. B. L- (3-Hydroxy-4-methoxyphenyl)-acetyl-carbinol, aus den entsprechenden Aldehyden mit Hilfe eines fermentativen Verfahrens unter Verwendung von Hefe herzustellen. It is known from US Pat. No. 1 962 476, optically active aryl acetyl carbinols, e.g. B. L- (3-Hydroxy-4-methoxyphenyl) -acetyl-carbinol, from the corresponding aldehydes with the help of a fermentative Method using yeast to produce.
Das stereospezifische Verfahren der Erfindung zur Herstellung von l(—)-3,4-Dimethoxyphenyl-acetylcarbinol ist dadurch gekennzeichnet, daß man Veratraldehyd mit einer wachsenden Kultur von Aerobacter aerogenes A. T. C. C. Nr. 211 in inniger Berührung zur Umsetzung bringt, das dabei gebildete l(—)-3,4-Dimethoxyphenylacetyl-carbinol mit einem mit Wasser nicht mischbaren Lösungsmittel extrahiert und auf bekannte Weise gewinnt.The stereospecific process of the invention for the preparation of l (-) - 3,4-dimethoxyphenyl-acetylcarbinol is characterized in that veratraldehyde with a growing culture of Aerobacter aerogenic A. T. C. C. No. 211 brings into intimate contact with the reaction, the l (-) - 3,4-dimethoxyphenylacetyl-carbinol formed in the process extracted with a water-immiscible solvent and recovered in a known manner.
Die bekannten Verfahren zur Herstellung von L-οι-Methyl-3,4-dihydroxyphenylalanin haben den Nachteil, daß zu irgendeinem Zeitpunkt der Synthese eine Trennung der L-Form von der D-Form vorgenommen werden muß. Dagegen erhält man durch das erfindungsgemäße Verfahren nur die D-Form von 3,4-Dimethoxyphenylacetyl-carbinol. Die Umsetzung dieser Verbindung mit einem wasserlöslichen Cyanidsalz und Ammoniumcarbonat führt beispielsweise zum 4 - Carbamoyl - 4 - methyl - 5 - (3,4 - dimethoxyphenyl)-2-oxazolidinon, in welchem sich das asymmetrische Kohlenstoffatom, welches an den Carbinol-Substituenten gebunden ist, in der erwünschten L-Konfiguration befindet. Wenn man das genannte Oxazolidinonderivat unter Rückfluß mit Jodwasserstoff und rotem Phosphor in wäßriger Essigsäure erhitzt, erhält man L-a-Methyl-3,4-dihydroxyphenylalanin.The known processes for the preparation of L -οι -Methyl -3,4-dihydroxyphenylalanine have the disadvantage that the L-form must be separated from the D-form at some point in the synthesis. In contrast, the process according to the invention only gives the D-form of 3,4-dimethoxyphenylacetyl-carbinol. The reaction of this compound with a water-soluble cyanide salt and ammonium carbonate leads, for example, to 4 - carbamoyl - 4 - methyl - 5 - (3,4 - dimethoxyphenyl) -2-oxazolidinone, in which there is the asymmetric carbon atom which is bonded to the carbinol substituent , is in the desired L-configuration. If the oxazolidinone derivative mentioned is heated under reflux with hydrogen iodide and red phosphorus in aqueous acetic acid, La-methyl-3,4-dihydroxyphenylalanine is obtained.
Das erfindungsgemäße Verfahren wird im allgemeinen bei etwa 25 bis 300C durchgeführt. Die hergestellte Verbindung trennt man anschließend von der Fermentationsbrühe durch Extraktion ab und gewinnt sie auf bekannte Weise.The process according to the invention is generally carried out at from about 25 to 30 ° C. The compound produced is then separated from the fermentation broth by extraction and is recovered in a known manner.
Das erfindungsgemäße Verfahren läuft etwa folgendermaßen ab:The method according to the invention proceeds roughly as follows:
Man impft ein geeignetes steriles Nährmedium, welches assimilierbaren Kohlenstoff und Stickstoff enthält, mit Aerobacter aerogenes A. T. C. C. Nr. 211 und belüftet und bewegt, bis ein erhebliches Wachstum des Mikroorganismus eintritt. Im allgemeinen wird hierzu ein Zeitraum von 1 bis 7 Tagen benötigt. Geeignete Medien für das erfindungsgemäße Verfahren sind in den nachfolgenden Tabellen angegeben. Medium IInoculate a suitable sterile nutrient medium which contains assimilable carbon and nitrogen contains, with Aerobacter aerogenes A. T. C. C. No. 211 and aerated and agitated until substantial growth of the microorganism occurs. In general, a period of 1 to 7 days is required for this. Suitable media for the process according to the invention are given in the tables below. Medium I.
Melasse 6 gMolasses 6 g
Wasser ausreichend für 100 mlWater sufficient for 100 ml
pH mit Phosphorsäure auf 5,5 eingestellt
Medium IIpH adjusted to 5.5 with phosphoric acid
Medium II
Handelsüblicher Hefeextrakt 20 gCommercial yeast extract 20 g
Dextrose 20 gDextrose 20 g
MgSO4-7H2O 0,5 gMgSO 4 -7H 2 O 0.5 g
KH2PO4 0,2 gKH 2 PO 4 0.2 g
Na2HPO4 0,2 gNa 2 HPO 4 0.2 g
Wasser ausreichend für 1,0 LiterWater sufficient for 1.0 liter
pH eingestellt auf 7pH adjusted to 7
Anschließend an die Wachstumsperiode fügt man Veratraldehyd in einer Konzentration von etwa 1 bis 10 g der Verbindung je Liter Medium zu und läßt das Gemisch unter Bewegung bei etwa 28 0C während einer Zeitspanne von 1 bis 10 Stunden brüten.Following the growth period, veratraldehyde is added in a concentration of about 1 to 10 g of the compound per liter of medium and the mixture is allowed to incubate with agitation at about 28 ° C. for a period of 1 to 10 hours.
Anschließend an die Brut-Periode extrahiert man die fermentierte Brühe, welche die erwünschte Verbindung zusammen mit anderen Stoffwechselprodukten enthält, mit einem mit Wasser nicht mischbaren Lösungsmittel für l(—)-3,4-Dimethoxyphenyl-acetyl-carbinol, z. B. mit einem Ester einer niederen aliphatischen Säure, vorzugsweise mit Äthylacetat.Subsequent to the breeding period, the fermented broth, which contains the desired compound, is extracted together with other metabolic products, with a water-immiscible solvent for l (-) - 3,4-dimethoxyphenyl-acetyl-carbinol, e.g. B. with an ester of a lower aliphatic Acid, preferably with ethyl acetate.
Der Lösungsmittelextrakt enthält zusätzlich zu dem erwünschten l(—)-3,4-Dimethoxyphenyl-acetyl-carbinol nicht umgesetzten Aldehyd ebenso wie den entsprechenden substituierten Benzylalkohol und die substituierte Benzoesäure. Man trennt l(—)-3,4-Dimethoxyphenyl-acetyl-carbinol von den verwandten Verbindungen durch Verfahren ab, wie Verteilungschromatographie an einem inerten Material, z. B. Diatomeenerde, fraktionierte Kristallisation oder Extraktion mit wäßriger Natriumbisulfitlösung.The solvent extract contains in addition to the desired l (-) - 3,4-dimethoxyphenyl-acetyl-carbinol unreacted aldehyde as well as the corresponding substituted benzyl alcohol and the substituted Benzoic acid. 1 (-) - 3,4-Dimethoxyphenyl-acetyl-carbinol is separated from the related compounds by methods such as partition chromatography on an inert material, e.g. B. Diatomaceous earth, fractional crystallization or extraction with aqueous sodium bisulfite solution.
Ein Fermentationsmedium, welches die Zusammensetzung des Mediums II besitzt, wird mit einem Stamm von Aerobacter aerogenes A. T. C. C. Nr. 211 beimpft. Das Medium wird anschließend gelüftet und bei 280C annähernd 48 Stunden bewegt, um ein optimales Wachstum des Pilzes zu erreichen. Belüftung und Bewegung werden eingestellt und dem Medium Veratraldehyd in einer Konzentration von 4 g je Liter Medium zugefügt. Anschließend an die Zugabe des Veratraldehyds belüftet und bewegt man das Medium neuerlich bei 28 0C für eine Zeitspanne von etwa 7 Stunden.A fermentation medium having the composition of Medium II is inoculated with a strain of Aerobacter aerogenes ATCC No. 211. The medium is then ventilated and agitated at 28 ° C. for approximately 48 hours in order to achieve optimal growth of the fungus. Aeration and agitation are stopped and veratraldehyde is added to the medium in a concentration of 4 g per liter of medium. Then vented to the addition of the Veratraldehyds and moves to the medium again at 28 0 C for a period of about 7 hours.
Anschließend an die Brut-Periode filtriert man die Fermentationsflüssigkeit, um die Zellkörper abzutrennen, und extrahiert mit Äthylacetat. Den Äthylacetat-Extrakt, welcher das Produkt enthält, extrahiert man mit wäßriger Bisulfit-Lösung und unterwirft ihn der Verteilungschromatographie an einer Säule aus Diatomeenerde, wobei man als bewegliche Phase ein Lösungsmittel-System aus Petroläther, Benzol, Methylalkohol, Wasser im Verhältnis 6:4:5:5 verwendet. Das erhaltene Material ist L-3,4-Dimethoxyphenylacetyl-carbinol, im wesentlichen frei von Veratraldehyd und Veratrylalkohol.After the incubation period, the fermentation liquid is filtered to separate the cell bodies, and extracted with ethyl acetate. The ethyl acetate extract containing the product is extracted one with aqueous bisulfite solution and subjects it to partition chromatography on a column Diatomaceous earth, with a solvent system consisting of petroleum ether, benzene, methyl alcohol, Water used in a ratio of 6: 4: 5: 5. The material obtained is L-3,4-dimethoxyphenylacetyl-carbinol, essentially free from verataldehyde and veratryl alcohol.
Das Öl zeigt das folgende kernmagnetische Spektrum: The oil shows the following nuclear magnetic spectrum:
(Aceton-de)TMS
(Acetone-d e )
4,86
5,23
6,20
7,943.01
4.86
5.23
6.20
7.94
d (/ = 3,6)
S
Sd (/ = 3.6)
d (/ = 3.6)
S.
S.
> CHOH
>CHOH
-OCH3
— CO — CH3 Aryl
> CHOH
> CHOH
-OCH 3
- CO - CH 3
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39050264A | 1964-08-19 | 1964-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1518029B1 true DE1518029B1 (en) | 1971-02-11 |
Family
ID=23542721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651518029 Pending DE1518029B1 (en) | 1964-08-19 | 1965-08-18 | Stereospecific process for the production of l (-) - 3,4-Dimethoxyphenyl-acetyl-carbinol |
Country Status (5)
| Country | Link |
|---|---|
| BR (1) | BR6572223D0 (en) |
| CH (1) | CH454162A (en) |
| DE (1) | DE1518029B1 (en) |
| GB (1) | GB1118293A (en) |
| NL (1) | NL6510879A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201118293D0 (en) | 2011-10-24 | 2011-12-07 | Sec Dep For Business Innovation & Skills The | Electrochemical assay |
-
1965
- 1965-07-14 CH CH989065A patent/CH454162A/en unknown
- 1965-08-12 GB GB3459965A patent/GB1118293A/en not_active Expired
- 1965-08-18 DE DE19651518029 patent/DE1518029B1/en active Pending
- 1965-08-18 BR BR17222365A patent/BR6572223D0/en unknown
- 1965-08-19 NL NL6510879A patent/NL6510879A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6510879A (en) | 1966-02-21 |
| CH454162A (en) | 1968-04-15 |
| GB1118293A (en) | 1968-06-26 |
| BR6572223D0 (en) | 1973-08-14 |
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