JPH0515701B2 - - Google Patents

Info

Publication number: JPH0515701B2
Authority: JP; Japan
Prior art keywords: amino; dimethoxyphenyl; methyl; propionitrile; acid
Prior art date: 1985-06-06
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

Application number

JP12150485A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61280461A (ja

Inventor

Ryoichi Hasegawa

Hiroaki Oono

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nippon Kayaku Co Ltd

Original Assignee

Nippon Kayaku Co Ltd

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.)

1985-06-06

Filing date

1985-06-06

Publication date

1993-03-02

1985-06-06 Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd

1985-06-06 Priority to JP12150485A priority Critical patent/JPS61280461A/ja

1986-12-11 Publication of JPS61280461A publication Critical patent/JPS61280461A/ja

1993-03-02 Publication of JPH0515701B2 publication Critical patent/JPH0515701B2/ja

Status Granted legal-status Critical Current

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)

JP12150485A 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 Granted JPS61280461A (ja)

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)

* Cited by examiner, † Cited by third party
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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JP3125101B2 (ja)	2001-01-15	光学異性ヒダントインの分割方法
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JPH09143128A (ja)	1997-06-03	光学活性１−フェニルエチルアミンの製造法
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JP3284605B2 (ja)	2002-05-20	光学活性１−（１−ナフチル）エチルアミンの製造法
JPH0665657B2 (ja)	1994-08-24	光学活性マンデル酸の製法
KR880000038B1 (ko)	1988-02-20	α-L-아스파틸-L-페닐알라닌 메틸 에스테르의 정제방법
JPH0784433B2 (ja)	1995-09-13	Ｎ−カルバモイルメチオニンの光学分割法
JP2003146943A (ja)	2003-05-21	光学活性２−ヒドロキシ−３−ニトロプロピオン酸の製造方法
JPS6261584B2 (de)	1987-12-22