CH398631A - Verfahren zur Herstellung von a-(niedrig Alkyl)-B-(3,4-dioxyphenyl)-alaninen - Google Patents

Verfahren zur Herstellung von a-(niedrig Alkyl)-B-(3,4-dioxyphenyl)-alaninen

Info

Publication number: CH398631A
Authority: CH; Switzerland
Prior art keywords: compound; formula; oxy; methyl; methoxyphenyl
Prior art date: 1960-05-09

Application number

CH532661A

Other languages

German (de)

English (en)

Inventor

Sletzinger Meyer

Original Assignee

Merck & Co Inc

Priority date (The priority date 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 date listed.)

1960-05-09

Filing date

1961-05-05

Publication date

1966-03-15

1961-05-05 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1966-03-15 Publication of CH398631A publication Critical patent/CH398631A/de

Links

238000000034 method Methods 0.000 title claims description 30
235000004279 alanine Nutrition 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 8
125000000217 alkyl group Chemical group 0.000 title claims description 6
150000001295 alanines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 28
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 17
239000000047 product Substances 0.000 claims description 17
229940091173 hydantoin Drugs 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
239000012736 aqueous medium Substances 0.000 claims description 10
238000010992 reflux Methods 0.000 claims description 10
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 10
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 9
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 9
235000012141 vanillin Nutrition 0.000 claims description 9
239000001099 ammonium carbonate Substances 0.000 claims description 6
235000012501 ammonium carbonate Nutrition 0.000 claims description 6
-1 compound ammonium carbonate Chemical class 0.000 claims description 6
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 5
229910052742 iron Inorganic materials 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
239000002609 medium Substances 0.000 claims description 2
238000006386 neutralization reaction Methods 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
239000000243 solution Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
FDLWTEUMNRJFCS-ALCCZGGFSA-N 2-methoxy-4-[(z)-2-nitroprop-1-enyl]phenol Chemical compound COC1=CC(\C=C(\C)[N+]([O-])=O)=CC=C1O FDLWTEUMNRJFCS-ALCCZGGFSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
229910001863 barium hydroxide Inorganic materials 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
159000000009 barium salts Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical compound CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 1
ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 description 1
WCGDQFYUAYIZOI-UHFFFAOYSA-N 2-methoxy-4-(2-nitrobut-1-enyl)phenol Chemical compound CCC([N+]([O-])=O)=CC1=CC=C(O)C(OC)=C1 WCGDQFYUAYIZOI-UHFFFAOYSA-N 0.000 description 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000001469 hydantoins Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH532661A 1960-05-09 1961-05-05 Verfahren zur Herstellung von a-(niedrig Alkyl)-B-(3,4-dioxyphenyl)-alaninen CH398631A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2749360A	1960-05-09	1960-05-09

Publications (1)

Publication Number	Publication Date
CH398631A true CH398631A (de)	1966-03-15

Family

ID=21838049

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH532661A CH398631A (de)	1960-05-09	1961-05-05	Verfahren zur Herstellung von a-(niedrig Alkyl)-B-(3,4-dioxyphenyl)-alaninen

Country Status (3)

Country	Link
BE (1)	BE603545A (fr)
CH (1)	CH398631A (fr)
GB (1)	GB940486A (fr)

1961
- 1961-05-03 GB GB1607261A patent/GB940486A/en not_active Expired
- 1961-05-05 CH CH532661A patent/CH398631A/de unknown
- 1961-05-08 BE BE603545A patent/BE603545A/fr unknown

Also Published As

Publication number	Publication date
GB940486A (en)	1963-10-30
BE603545A (fr)	1961-11-08

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DE1620694B2 (de)	1981-07-16	Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren
DE1795841C3 (de)	1979-07-12	H2'-Chlor)-benzyl-2-di-sec.-butylamino-acetyl-pyrrol, seine Salze und Verfahren zu deren Herstellung
DE2753828A1 (de)	1978-06-08	Verfahren zur herstellung von alpha-aminoamiden
DE3043159C2 (de)	1982-12-09	Cyclische Acetale des Glutaminsäure-&gamma;-semialdehyds, Verfahren zu deren Herstellung und ihre Verwendung
EP0110031B1 (fr)	1987-04-01	Procédé de préparation de 1,2-dioles
AT225182B (de)	1963-01-10	Verfahren zur Herstellung von α-Niederalkyl-β-(3,4-dihydroxyphenyl)-alaninen
DE1570013B1 (de)	1970-07-02	1,4-Bis-(phenoxyacetyl)-piperazinderivate und Verfahren zu ihrer Herstellung
EP0002807A1 (fr)	1979-07-11	Procédé de préparation d'alpha-hydroxy-bêta,bêta-diméthyl-gamma-butyrolactone
DE2944257A1 (de)	1980-05-14	Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl) guanidin
DE1518009C2 (de)	1973-01-04	alpha-Aminomethyl-S^-dihydroxyphenylalanin, Alkalisalze und Säureadditionssalze dieser Verbindung, Verfahren zur Herstellung dieser Verbindungen und Arzneimittel, enthaltend eine dieser Verbindungen
EP0024682B1 (fr)	1982-12-22	Procédé de préparation de n-propyl-n-propylidène-acétamide ou de di-n-propyl-acétamide
DE805523C (de)	1951-05-21	Verfahren zur Herstellung von Histaminen
DE2617967C3 (de)	1978-11-02	Verfahren zur Herstellung von 2,4-Diamino-5-benzylpyrimidinen
AT225181B (de)	1963-01-10	Verfahren zur Herstellung von neuen Phenylalaninderivaten
DE3538747A1 (de)	1986-08-14	Verfahren zur herstellung von pyrrolidin-derivaten
AT232500B (de)	1964-03-25	Verfahren zur Herstellung von neuen Phenylalaninderivaten
DE69914719T2 (de)	2004-07-29	Verfahren zur Herstellung von 1-[(Cyclopent-3-en-1-yl)-methyl]-5-ethyl-6-(3,5-dimethylbenzoyl)-2,4-pyrimidindion
DE867245C (de)	1953-02-16	Verfahren zur Herstellung von Monoalkylpiperazinen
AT217025B (de)	1961-09-11	Verfahren zur Herstellung von neuen α-Aminoisobutyrophenonverbindungen und deren Säureadditionssalzen
CH389639A (de)	1965-03-31	Verfahren zur Herstellung von Phenylalanin-Derivaten
CH433375A (de)	1967-04-15	Verfahren zur Herstellung von neuen Aminosäuren
DE2924334C2 (fr)	1987-10-29
DE2318566C3 (de)	1976-10-14	3-Alkoxy-5-substituierte Phenylessigsäuren
DE1445652A1 (de)	1969-01-16	Neue Glutarimide und Verfahren zu deren Herstellung
AT204045B (de)	1959-06-25	Verfahren zur Herstellung von neuen Piperazinderivaten und von deren Salzen