JPH0515701B2 - - Google Patents
Info
- Publication number
- JPH0515701B2 JPH0515701B2 JP12150485A JP12150485A JPH0515701B2 JP H0515701 B2 JPH0515701 B2 JP H0515701B2 JP 12150485 A JP12150485 A JP 12150485A JP 12150485 A JP12150485 A JP 12150485A JP H0515701 B2 JPH0515701 B2 JP H0515701B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- dimethoxyphenyl
- methyl
- propionitrile
- 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.)
- Expired - Lifetime
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 16
- 229960001270 d- tartaric acid Drugs 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 12
- 235000010755 mineral Nutrition 0.000 claims description 12
- 239000011707 mineral Substances 0.000 claims description 12
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 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 claims description 6
- 229940095064 tartrate Drugs 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- QYPVUSRSPJQLAY-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2-methylpropanenitrile Chemical compound COC1=CC=C(CC(C)C#N)C=C1OC QYPVUSRSPJQLAY-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Chemical class 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 4
- -1 (dimethoxyphenyl)-2-methylpropionitrile Chemical compound 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 229960002510 mandelic acid Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010520 demethylation reaction Methods 0.000 description 3
- 239000012456 homogeneous solution Substances 0.000 description 3
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-M D-tartrate(1-) Chemical compound OC(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 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 1
- 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 description 1
- PGQTYXFMSZUGOW-UHFFFAOYSA-N 2-methyl-2-phenylpropanenitrile Chemical compound N#CC(C)(C)C1=CC=CC=C1 PGQTYXFMSZUGOW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HELHAJAZNSDZJO-OTWIGTIJSA-L disodium;(2s,3s)-2,3-dihydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O HELHAJAZNSDZJO-OTWIGTIJSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12150485A JPS61280461A (ja) | 1985-06-06 | 1985-06-06 | L−2−アミノ−3−(3,4−ジメトキシフエニル)−2−メチルプロピオニトリルの製造法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP12150485A JPS61280461A (ja) | 1985-06-06 | 1985-06-06 | L−2−アミノ−3−(3,4−ジメトキシフエニル)−2−メチルプロピオニトリルの製造法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61280461A JPS61280461A (ja) | 1986-12-11 |
JPH0515701B2 true JPH0515701B2 (de) | 1993-03-02 |
Family
ID=14812825
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP12150485A Granted JPS61280461A (ja) | 1985-06-06 | 1985-06-06 | L−2−アミノ−3−(3,4−ジメトキシフエニル)−2−メチルプロピオニトリルの製造法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61280461A (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007284349A (ja) * | 2004-07-27 | 2007-11-01 | Ajinomoto Co Inc | モナティンまたはその塩の製造方法 |
CN104628600B (zh) * | 2013-11-11 | 2016-08-24 | 上海医药工业研究院 | 一种(s)-甲基多巴中间体化合物的制备方法 |
-
1985
- 1985-06-06 JP JP12150485A patent/JPS61280461A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS61280461A (ja) | 1986-12-11 |
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