JPH0576465B2 - - Google Patents
Info
- Publication number
- JPH0576465B2 JPH0576465B2 JP11539385A JP11539385A JPH0576465B2 JP H0576465 B2 JPH0576465 B2 JP H0576465B2 JP 11539385 A JP11539385 A JP 11539385A JP 11539385 A JP11539385 A JP 11539385A JP H0576465 B2 JPH0576465 B2 JP H0576465B2
- Authority
- JP
- Japan
- Prior art keywords
- methylalanine
- hours
- reaction
- hydrochloric acid
- dimethoxyphenyl
- 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 - Lifetime
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 63
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 26
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 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 claims description 12
- 230000001335 demethylating effect Effects 0.000 claims description 3
- QCCQWLWXLUTSAK-LBPRGKRZSA-N (2s)-2-amino-3-(3,4-dimethoxyphenyl)-2-methylpropanoic acid Chemical compound COC1=CC=C(C[C@](C)(N)C(O)=O)C=C1OC QCCQWLWXLUTSAK-LBPRGKRZSA-N 0.000 claims description 2
- GEFHJACVQBNFFP-UHFFFAOYSA-N 2-amino-3-(3,4-dimethoxyphenyl)-2-methylpropanenitrile Chemical compound COC1=CC=C(CC(C)(N)C#N)C=C1OC GEFHJACVQBNFFP-UHFFFAOYSA-N 0.000 claims description 2
- NLRUDGHSXOEXCE-PPHPATTJSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;hydrochloride Chemical compound Cl.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 NLRUDGHSXOEXCE-PPHPATTJSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000013078 crystal Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 238000004040 coloring Methods 0.000 description 6
- 238000010520 demethylation reaction Methods 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 ammonium halide Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VWZUIIYOJGQRBR-UHFFFAOYSA-N 2-(3,4-dihydroxyanilino)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC1=CC=C(O)C(O)=C1 VWZUIIYOJGQRBR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- CJCSPKMFHVPWAR-SNVBAGLBSA-N (2r)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid Chemical compound OC(=O)[C@@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-SNVBAGLBSA-N 0.000 description 1
- KUBJFKQGURRWJL-UHFFFAOYSA-N 2-(3,4-dimethoxyanilino)-2-methylpropanoic acid Chemical compound COC1=CC=C(NC(C)(C)C(O)=O)C=C1OC KUBJFKQGURRWJL-UHFFFAOYSA-N 0.000 description 1
- OEWDSMNBHDNSTP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-methylpropanenitrile Chemical compound COC1=CC=C(C(C)(C)C#N)C=C1OC OEWDSMNBHDNSTP-UHFFFAOYSA-N 0.000 description 1
- GNOCKUYGCRRLQP-RUCXOUQFSA-N CN[C@@H](C)C(=O)O.CN[C@@H](C)C(=O)O Chemical compound CN[C@@H](C)C(=O)O.CN[C@@H](C)C(=O)O GNOCKUYGCRRLQP-RUCXOUQFSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012649 demethylating agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000002002 slurry Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11539385A JPS61275253A (ja) | 1985-05-30 | 1985-05-30 | ３−（３，４−ジヒドロキシフエニル）−２−メチルアラニンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11539385A JPS61275253A (ja) | 1985-05-30 | 1985-05-30 | ３−（３，４−ジヒドロキシフエニル）−２−メチルアラニンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61275253A JPS61275253A (ja) | 1986-12-05 |
| JPH0576465B2 true JPH0576465B2 (enrdf_load_stackoverflow) | 1993-10-22 |
Family
ID=14661440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11539385A Granted JPS61275253A (ja) | 1985-05-30 | 1985-05-30 | ３−（３，４−ジヒドロキシフエニル）−２−メチルアラニンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61275253A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1226902B (it) * | 1988-07-12 | 1991-02-21 | Mini Ricerca Scient Tecnolog | Processo per la sintesi del levodopa |
-
1985
- 1985-05-30 JP JP11539385A patent/JPS61275253A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61275253A (ja) | 1986-12-05 |