JPH0569818B2 - - Google Patents
Info
- Publication number
- JPH0569818B2 JPH0569818B2 JP62153038A JP15303887A JPH0569818B2 JP H0569818 B2 JPH0569818 B2 JP H0569818B2 JP 62153038 A JP62153038 A JP 62153038A JP 15303887 A JP15303887 A JP 15303887A JP H0569818 B2 JPH0569818 B2 JP H0569818B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxybutyronitrile
- chloro
- epichlorohydrin
- reaction
- chem
- 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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- LHBPNZDUNCZWFL-UHFFFAOYSA-N 4-chloro-3-hydroxybutanenitrile Chemical compound ClCC(O)CC#N LHBPNZDUNCZWFL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal cyanide Chemical class 0.000 claims description 4
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical group [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 2
- 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 claims description 2
- 238000000034 method Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229960001518 levocarnitine Drugs 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LHBPNZDUNCZWFL-SCSAIBSYSA-N (3r)-4-chloro-3-hydroxybutanenitrile Chemical compound ClC[C@H](O)CC#N LHBPNZDUNCZWFL-SCSAIBSYSA-N 0.000 description 3
- BYJAJQGCMSBKPB-UHFFFAOYSA-N 3-hydroxybutanenitrile Chemical compound CC(O)CC#N BYJAJQGCMSBKPB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BRLQWZUYTZBJKN-VKHMYHEASA-N (-)-Epichlorohydrin Chemical compound ClC[C@H]1CO1 BRLQWZUYTZBJKN-VKHMYHEASA-N 0.000 description 2
- YQGDEPYYFWUPGO-GSVOUGTGSA-N (3r)-4-amino-3-hydroxybutanoic acid Chemical compound NC[C@H](O)CC(O)=O YQGDEPYYFWUPGO-GSVOUGTGSA-N 0.000 description 2
- NHSSTOSZJANVEV-UHFFFAOYSA-N 2-hydroxybutanenitrile Chemical compound CCC(O)C#N NHSSTOSZJANVEV-UHFFFAOYSA-N 0.000 description 2
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229960004203 carnitine Drugs 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- YQGDEPYYFWUPGO-UHFFFAOYSA-N gamma-amino-beta-hydroxybutyric acid Chemical compound [NH3+]CC(O)CC([O-])=O YQGDEPYYFWUPGO-UHFFFAOYSA-N 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BAPRUDZDYCKSOQ-RITPCOANSA-N (2s,4r)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acid Chemical compound CC(=O)N1C[C@H](O)C[C@H]1C(O)=O BAPRUDZDYCKSOQ-RITPCOANSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 125000001549 ceramide group Chemical group 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229960001855 mannitol Drugs 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- FJMMZJZTJGGXHX-UHFFFAOYSA-N potassium sodium dicyanide Chemical compound [K+].[C-]#N.[Na+].[C-]#N FJMMZJZTJGGXHX-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance 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 |
|---|---|---|---|
| JP15303887A JPS63316758A (ja) | 1987-06-18 | 1987-06-18 | ４−クロル−３−ヒドロキシブチロニトリルの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15303887A JPS63316758A (ja) | 1987-06-18 | 1987-06-18 | ４−クロル−３−ヒドロキシブチロニトリルの製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63316758A JPS63316758A (ja) | 1988-12-26 |
| JPH0569818B2 true JPH0569818B2 (el) | 1993-10-01 |
Family
ID=15553617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15303887A Granted JPS63316758A (ja) | 1987-06-18 | 1987-06-18 | ４−クロル−３−ヒドロキシブチロニトリルの製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63316758A (el) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009122997A1 (ja) | 2008-04-02 | 2009-10-08 | 株式会社カネカ | （ｓ）－３－（１－シアノ－１，１－ジフェニルメチル）－ピロリジンの製造法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210031A (en) * | 1989-07-20 | 1993-05-11 | Nitto Chemical Industry Co., Ltd. | Process for the production of R(-)-4-halo-3-hydroxybutyronitrile |
| JPH04124157A (ja) * | 1990-09-12 | 1992-04-24 | Daiso Co Ltd | 光学活性４―クロロ―３―ヒドロキシブタン酸及びそのエステルの製法 |
| JP2734876B2 (ja) * | 1992-05-14 | 1998-04-02 | ダイソー株式会社 | 光学活性４−クロロ−３−ヒドロキシブチロニトリルの製造方法 |
| JPH11193285A (ja) * | 1997-12-26 | 1999-07-21 | Dai Ichi Seiyaku Co Ltd | 二環性複素環チオール化合物の製造方法 |
| KR100491809B1 (ko) * | 2002-11-27 | 2005-05-27 | 주식회사 알에스텍 | 3-치환된-3'-하이드록시프로피오나이트릴의 제조방법 |
| KR20040090062A (ko) * | 2003-04-16 | 2004-10-22 | 주식회사 엘지생명과학 | 4-클로로-3-히드록시부탄산 에스테르의 제조방법 |
| EP1725521A4 (en) * | 2004-03-13 | 2007-07-25 | Rstech Corp | PROCESS PREPARATION OF 3'-HYDROXYPROPIONITRILE SUBSTITUTED IN 3 |
| JP2008067626A (ja) * | 2006-09-13 | 2008-03-27 | Mitsubishi Rayon Co Ltd | ４−ハロ−３−ヒドロキシブチルアミドの製造方法 |
| CN100408555C (zh) * | 2006-09-15 | 2008-08-06 | 四川省天然气化工研究院 | 4-氯-3-羟基丁腈的制备方法 |
| JP2008148637A (ja) * | 2006-12-19 | 2008-07-03 | Mitsubishi Rayon Co Ltd | ４−ハロ−３−ヒドロキシブチルアミドの製造方法 |
-
1987
- 1987-06-18 JP JP15303887A patent/JPS63316758A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009122997A1 (ja) | 2008-04-02 | 2009-10-08 | 株式会社カネカ | （ｓ）－３－（１－シアノ－１，１－ジフェニルメチル）－ピロリジンの製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63316758A (ja) | 1988-12-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term | ||
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20071001 Year of fee payment: 14 |