DE1236524C2 - Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin - Google Patents
Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alaninInfo
- Publication number
- DE1236524C2 DE1236524C2 DE19641236524 DE1236524A DE1236524C2 DE 1236524 C2 DE1236524 C2 DE 1236524C2 DE 19641236524 DE19641236524 DE 19641236524 DE 1236524 A DE1236524 A DE 1236524A DE 1236524 C2 DE1236524 C2 DE 1236524C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- dimethoxybenzyl
- acetic acid
- phenyl
- hydantoin
- 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
- 238000000034 method Methods 0.000 title claims description 15
- CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- HAJABMGNYPPULO-UHFFFAOYSA-N acetic acid;isocyanic acid Chemical class N=C=O.CC(O)=O HAJABMGNYPPULO-UHFFFAOYSA-N 0.000 claims 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 229940091173 hydantoin Drugs 0.000 description 3
- -1 3,4-dihydroxyphenyl Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000001469 hydantoins Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KZVRXPPUJQRGFN-UHFFFAOYSA-N N-carbamoylglycine Chemical class NC(=O)NCC(O)=O KZVRXPPUJQRGFN-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- QVTMGLKIERGFFS-UHFFFAOYSA-N acetic acid;isocyanatoethane Chemical compound CC(O)=O.CCN=C=O QVTMGLKIERGFFS-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- MPCQNSCUKOECNW-UHFFFAOYSA-N butan-1-ol;ethanol Chemical compound CCO.CCCCO MPCQNSCUKOECNW-UHFFFAOYSA-N 0.000 description 1
- 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL126377D NL126377C (enrdf_load_stackoverflow) | 1964-07-31 | ||
| DE19641236524 DE1236524C2 (de) | 1964-07-31 | 1964-07-31 | Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin |
| IL2404265A IL24042A (en) | 1964-07-31 | 1965-07-27 | Process for the preparation of l-(-)-alpha-methyl-beta-(3,4-dihydroxy-phenyl)-alanine |
| FI182665A FI43440C (fi) | 1964-07-31 | 1965-07-28 | L-(-)-alfa-metyyli-beeta-(3,4-dihydroksi-fenyyli)-alaniinin valmistusmenetelmä |
| LU49191A LU49191A1 (enrdf_load_stackoverflow) | 1964-07-31 | 1965-07-28 | |
| FR26486A FR1445051A (fr) | 1964-07-31 | 1965-07-29 | Procédé pour la préparation de l-(-)-alpha-méthyl-beta-(3, 4-dihydroxy-phényl)-alanine |
| CH1063865A CH451187A (de) | 1964-07-31 | 1965-07-29 | Verfahren zur Herstellung von L-(-)-a-Methyl-B-(3,4-dihydroxy-phenyl)-alanin |
| NL6509816A NL6509816A (enrdf_load_stackoverflow) | 1964-07-31 | 1965-07-29 | |
| GB3271465A GB1040169A (en) | 1964-07-31 | 1965-07-30 | Process for the preparation of l-(-)-ª‡-methyl-ª‰-(3,4-dihydroxy-phenyl)-alanine |
| BE667717D BE667717A (enrdf_load_stackoverflow) | 1964-07-31 | 1965-07-30 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19641236524 DE1236524C2 (de) | 1964-07-31 | 1964-07-31 | Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin |
| DEB0077917 | 1964-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1236524B DE1236524B (enrdf_load_stackoverflow) | 1973-10-04 |
| DE1236524C2 true DE1236524C2 (de) | 1973-10-04 |
Family
ID=25750877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641236524 Expired DE1236524C2 (de) | 1964-07-31 | 1964-07-31 | Verfahren zur herstellung von l-(-) -alpha-methyl-beta-(3,4-dihydroxy-phenyl)alanin |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE667717A (enrdf_load_stackoverflow) |
| CH (1) | CH451187A (enrdf_load_stackoverflow) |
| DE (1) | DE1236524C2 (enrdf_load_stackoverflow) |
| FI (1) | FI43440C (enrdf_load_stackoverflow) |
| FR (1) | FR1445051A (enrdf_load_stackoverflow) |
| GB (1) | GB1040169A (enrdf_load_stackoverflow) |
| IL (1) | IL24042A (enrdf_load_stackoverflow) |
| LU (1) | LU49191A1 (enrdf_load_stackoverflow) |
| NL (2) | NL6509816A (enrdf_load_stackoverflow) |
-
0
- NL NL126377D patent/NL126377C/xx active
-
1964
- 1964-07-31 DE DE19641236524 patent/DE1236524C2/de not_active Expired
-
1965
- 1965-07-27 IL IL2404265A patent/IL24042A/xx unknown
- 1965-07-28 FI FI182665A patent/FI43440C/fi active
- 1965-07-28 LU LU49191A patent/LU49191A1/xx unknown
- 1965-07-29 CH CH1063865A patent/CH451187A/de unknown
- 1965-07-29 FR FR26486A patent/FR1445051A/fr not_active Expired
- 1965-07-29 NL NL6509816A patent/NL6509816A/xx unknown
- 1965-07-30 BE BE667717D patent/BE667717A/xx unknown
- 1965-07-30 GB GB3271465A patent/GB1040169A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE667717A (enrdf_load_stackoverflow) | 1966-01-31 |
| DE1236524B (enrdf_load_stackoverflow) | 1973-10-04 |
| NL126377C (enrdf_load_stackoverflow) | |
| FI43440C (fi) | 1971-04-13 |
| GB1040169A (en) | 1966-08-24 |
| IL24042A (en) | 1969-01-29 |
| NL6509816A (enrdf_load_stackoverflow) | 1966-02-01 |
| FI43440B (enrdf_load_stackoverflow) | 1970-12-31 |
| CH451187A (de) | 1968-05-15 |
| FR1445051A (fr) | 1966-07-08 |
| LU49191A1 (enrdf_load_stackoverflow) | 1965-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C2 | Grant after previous publication (2nd publication) |