CN107188808A - 一种4‑氨基‑3‑苯基丁酸盐酸盐的合成方法 - Google Patents
一种4‑氨基‑3‑苯基丁酸盐酸盐的合成方法 Download PDFInfo
- Publication number
- CN107188808A CN107188808A CN201710363910.XA CN201710363910A CN107188808A CN 107188808 A CN107188808 A CN 107188808A CN 201710363910 A CN201710363910 A CN 201710363910A CN 107188808 A CN107188808 A CN 107188808A
- Authority
- CN
- China
- Prior art keywords
- phenylbutyric acid
- amino
- methyl esters
- acid hydrochloride
- phenylbutyric
- 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.)
- Pending
Links
- 238000010189 synthetic method Methods 0.000 title abstract description 6
- CUVKGDMKCGZETK-UHFFFAOYSA-N 2-phenylbutanoic acid;hydrochloride Chemical compound Cl.CCC(C(O)=O)C1=CC=CC=C1 CUVKGDMKCGZETK-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title abstract 4
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 17
- XSYRYMGYPBGOPS-UHFFFAOYSA-N 4-amino-3-phenylbutanoic acid;hydrochloride Chemical compound [Cl-].OC(=O)CC(C[NH3+])C1=CC=CC=C1 XSYRYMGYPBGOPS-UHFFFAOYSA-N 0.000 claims description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- QGMLRHACACRFNN-UHFFFAOYSA-N methyl 4-amino-3-phenylbutanoate Chemical class COC(=O)CC(CN)C1=CC=CC=C1 QGMLRHACACRFNN-UHFFFAOYSA-N 0.000 claims description 8
- ZJFQGMLHRHGKEV-UHFFFAOYSA-N methyl 4-nitro-3-phenylbutanoate Chemical class COC(=O)CC(C[N+]([O-])=O)C1=CC=CC=C1 ZJFQGMLHRHGKEV-UHFFFAOYSA-N 0.000 claims description 8
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 8
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- DAFOCGYVTAOKAJ-UHFFFAOYSA-N phenibut Chemical compound OC(=O)CC(CN)C1=CC=CC=C1 DAFOCGYVTAOKAJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- PPIQQNDMGXNRFA-UHFFFAOYSA-N methyl 2-phenylbutanoate Chemical class COC(=O)C(CC)C1=CC=CC=C1 PPIQQNDMGXNRFA-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 238000011017 operating method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- GOEBEEJCYYXSFT-UHFFFAOYSA-N 2-phenylpentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C1=CC=CC=C1 GOEBEEJCYYXSFT-UHFFFAOYSA-N 0.000 description 1
- GMPNSKPTQXVWAF-UHFFFAOYSA-N 3-cyano-3-phenylpropanoic acid Chemical compound OC(=O)CC(C#N)C1=CC=CC=C1 GMPNSKPTQXVWAF-UHFFFAOYSA-N 0.000 description 1
- 150000005358 3-phenylpyrroles Chemical class 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 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
- 208000027601 Inner ear disease Diseases 0.000 description 1
- 208000007443 Neurasthenia Diseases 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 208000013200 Stress disease Diseases 0.000 description 1
- 208000003028 Stuttering Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 208000027491 vestibular disease Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
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CN201710363910.XA CN107188808A (zh) | 2017-05-22 | 2017-05-22 | 一种4‑氨基‑3‑苯基丁酸盐酸盐的合成方法 |
Applications Claiming Priority (1)
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CN201710363910.XA CN107188808A (zh) | 2017-05-22 | 2017-05-22 | 一种4‑氨基‑3‑苯基丁酸盐酸盐的合成方法 |
Publications (1)
Publication Number | Publication Date |
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CN107188808A true CN107188808A (zh) | 2017-09-22 |
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Family Applications (1)
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CN201710363910.XA Pending CN107188808A (zh) | 2017-05-22 | 2017-05-22 | 一种4‑氨基‑3‑苯基丁酸盐酸盐的合成方法 |
Country Status (1)
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CN (1) | CN107188808A (zh) |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU236479A1 (ru) * | 1967-05-20 | 1976-07-05 | Ленинградский Ордена Трудового Красного Знамени Государственный Педагогический Институт Им. А.И.Герцена | Способ получени хлогидрата - фенил - аминомасл ной кислоты |
EP0164852A1 (en) * | 1984-05-07 | 1985-12-18 | Warner-Lambert Company | 1-(Substituted-aryl)-Dihydro-1H-pyrrolizine-3,5-(2H,6H-)diones, a process for producing the compounds and a pharmaceutical composition comprising the compounds |
US4584313A (en) * | 1984-05-07 | 1986-04-22 | Warner-Lambert Company | (Substituted-phenyl)-5-oxo-2-pyrrolidinepropanoic acids and esters thereof, and use for reversing electroconvulsive shock-induced amnesia |
RU2146246C1 (ru) * | 1998-05-15 | 2000-03-10 | Гареев Гегель Амирович | СПОСОБ ПОЛУЧЕНИЯ ГИДРОХЛОРИДА γ-АМИНО-βФЕНИЛМАСЛЯНОЙ КИСЛОТЫ (ФЕНИБУТА) |
CN101033195A (zh) * | 2007-04-17 | 2007-09-12 | 安徽省郎溪县科联实业有限公司 | 4-氨基-3-苯基丁酸盐酸盐的制备方法 |
US20070270436A1 (en) * | 2006-05-22 | 2007-11-22 | Recordati Ireland Limited | Novel amino- and imino-alkylpiperazines |
CN103232356A (zh) * | 2013-05-15 | 2013-08-07 | 天津聚德科技有限公司 | 一种制备3-苯基-4-氨基丁酸盐酸盐的工艺 |
CN104402746A (zh) * | 2014-11-03 | 2015-03-11 | 陕西嘉禾植物化工有限责任公司 | 一种4-氨基-3-苯基丁酸盐酸盐的合成方法 |
CN104478745A (zh) * | 2014-11-03 | 2015-04-01 | 陕西嘉禾植物化工有限责任公司 | 一种4-氨基-3-苯基丁酸盐酸盐的合成方法 |
CN105153006A (zh) * | 2015-10-08 | 2015-12-16 | 常州强达宝成化工有限公司 | 4-苯基-2-吡咯烷酮的合成方法 |
-
2017
- 2017-05-22 CN CN201710363910.XA patent/CN107188808A/zh active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU236479A1 (ru) * | 1967-05-20 | 1976-07-05 | Ленинградский Ордена Трудового Красного Знамени Государственный Педагогический Институт Им. А.И.Герцена | Способ получени хлогидрата - фенил - аминомасл ной кислоты |
EP0164852A1 (en) * | 1984-05-07 | 1985-12-18 | Warner-Lambert Company | 1-(Substituted-aryl)-Dihydro-1H-pyrrolizine-3,5-(2H,6H-)diones, a process for producing the compounds and a pharmaceutical composition comprising the compounds |
US4584313A (en) * | 1984-05-07 | 1986-04-22 | Warner-Lambert Company | (Substituted-phenyl)-5-oxo-2-pyrrolidinepropanoic acids and esters thereof, and use for reversing electroconvulsive shock-induced amnesia |
RU2146246C1 (ru) * | 1998-05-15 | 2000-03-10 | Гареев Гегель Амирович | СПОСОБ ПОЛУЧЕНИЯ ГИДРОХЛОРИДА γ-АМИНО-βФЕНИЛМАСЛЯНОЙ КИСЛОТЫ (ФЕНИБУТА) |
US20070270436A1 (en) * | 2006-05-22 | 2007-11-22 | Recordati Ireland Limited | Novel amino- and imino-alkylpiperazines |
CN101033195A (zh) * | 2007-04-17 | 2007-09-12 | 安徽省郎溪县科联实业有限公司 | 4-氨基-3-苯基丁酸盐酸盐的制备方法 |
CN103232356A (zh) * | 2013-05-15 | 2013-08-07 | 天津聚德科技有限公司 | 一种制备3-苯基-4-氨基丁酸盐酸盐的工艺 |
CN104402746A (zh) * | 2014-11-03 | 2015-03-11 | 陕西嘉禾植物化工有限责任公司 | 一种4-氨基-3-苯基丁酸盐酸盐的合成方法 |
CN104478745A (zh) * | 2014-11-03 | 2015-04-01 | 陕西嘉禾植物化工有限责任公司 | 一种4-氨基-3-苯基丁酸盐酸盐的合成方法 |
CN105153006A (zh) * | 2015-10-08 | 2015-12-16 | 常州强达宝成化工有限公司 | 4-苯基-2-吡咯烷酮的合成方法 |
Non-Patent Citations (4)
Title |
---|
DIEGO GHISLIERI ETAL: "Chemical Assembly Systems: Layered Control for Divergent,Continuous, Multistep Syntheses of Active Pharmaceutical Ingredients", 《ANGEW. CHEM. INT. ED.》 * |
NAITO, TAKEAKI ETAL: "Radical cyclization in heterocycle synthesis. II. Total synthesis of (±)-anantine and (±)-isoanantine", 《CHEMICAL & PHARMACEUTICAL BULLETIN》 * |
POLLINI, G. P.ETAL: "Tetramethylguanidine-catalyzed addition of nitromethane to α,β-unsaturated carboxylic acid esters", 《SYNTHESIS》 * |
葛燕丽等: "哌啶酮类法尼基转移酶抑制剂的设计、合成及初步抗肿瘤活性研究", 《化学学报》 * |
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TA01 | Transfer of patent application right |
Effective date of registration: 20181217 Address after: 462499 Chemical Park of Southern Qingdao Road, Wuyang County Industrial Agglomeration Area, Luohe City, Henan Province Applicant after: Wuyang lelexin Biological Medicine Co Ltd Address before: 215634 Building D, No. 7 Guangdong Road, Zhangjiagang Free Trade Zone, Suzhou City, Jiangsu Province, 3rd Floor Applicant before: Jiangsu Swithin Biological Medicine Engineering Research Center Co., Ltd. Applicant before: Zhangjiagang Weisheng Biological Pharmaceutical Co., Ltd. Applicant before: Wuyang lelexin Biological Medicine Co Ltd |
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Application publication date: 20170922 |