MX342892B - Un procedimiento para sintetizar compuestos de p-hidroxifenilglicina levorrotatoria. - Google Patents
Un procedimiento para sintetizar compuestos de p-hidroxifenilglicina levorrotatoria.Info
- Publication number
- MX342892B MX342892B MX2013006993A MX2013006993A MX342892B MX 342892 B MX342892 B MX 342892B MX 2013006993 A MX2013006993 A MX 2013006993A MX 2013006993 A MX2013006993 A MX 2013006993A MX 342892 B MX342892 B MX 342892B
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- laevo
- synthesizing
- hydroxyphenylglycine
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 amine compound Chemical class 0.000 abstract 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 238000005935 nucleophilic addition reaction Methods 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/02—Addition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invención se refiere al campo de la síntesis química, en particular a un procedimiento para sintetizar compuestos de p-hidroxifenilglicina levorrotatoria, que elimina los procesos posteriores de resolución, los procesamientos de racemización, etc., simplifica las etapas operativas; y se eligen ácidos de molécula orgánica pequeña como catalizador en la segunda etapa, que no solo conduce a la realización de una producción industrializada, sino que también hace que el valor de ee de los productos finales sea del 88,1~98,0% determinando el catalizador, el disolvente de reacción, la sustancia reactiva, la temperatura de reacción y la duración de la reacción; se usa un disolvente no acuoso en la segunda etapa para evitar la descarga de agua residual que contiene fenol, por lo que se reduce la contaminación medioambiental.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2012/071159 WO2013120257A1 (zh) | 2012-02-15 | 2012-02-15 | 一种左旋对羟基苯甘氨酸类化合物的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
MX2013006993A MX2013006993A (es) | 2013-12-06 |
MX342892B true MX342892B (es) | 2016-10-18 |
Family
ID=48672096
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MX2013006993A MX342892B (es) | 2012-02-15 | 2012-02-15 | Un procedimiento para sintetizar compuestos de p-hidroxifenilglicina levorrotatoria. |
Country Status (7)
Country | Link |
---|---|
US (1) | US8940928B2 (es) |
JP (1) | JP5767346B2 (es) |
CA (1) | CA2818094C (es) |
ES (1) | ES2429431B2 (es) |
GB (1) | GB2503341B (es) |
MX (1) | MX342892B (es) |
WO (1) | WO2013120257A1 (es) |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3860631A (en) * | 1973-12-06 | 1975-01-14 | Smithkline Corp | Process for the preparation of n-acyl-2- and 4-hydroxyphenylglycines |
CH614928A5 (es) * | 1975-09-12 | 1979-12-28 | Nobel Hoechst Chimie | |
NL9000653A (nl) | 1990-03-21 | 1991-10-16 | Kessels Gerard | Werkwijze voor de bereiding van d-(-)-4-hydroxyfenylglycine en l-(+)-4-hydroxyfenylglycine, uitgaande van d.l.-4-hydroxyfenylglycine. |
NL9101380A (nl) * | 1991-08-13 | 1993-03-01 | Dsm Nv | Werkwijze voor de bereiding van een alfa-aminozuur, de overeenkomstige ester en amide. |
CN1072926A (zh) | 1992-11-19 | 1993-06-09 | 河北师范学院 | D-(-)-[4-r]-苯甘氨酸的制备方法 |
JPH10279541A (ja) * | 1997-04-02 | 1998-10-20 | Nippon Shokubai Co Ltd | 2−置換グリコール酸化合物及びその製造方法 |
CN100494165C (zh) | 2006-03-29 | 2009-06-03 | 宝山钢铁股份有限公司 | D-对羟基苯甘氨酸的制备方法 |
CN101362703B (zh) * | 2007-08-09 | 2011-11-16 | 谢建中 | 对羟基苯甘氨酸合成技术 |
CN100519514C (zh) | 2008-03-13 | 2009-07-29 | 河北宏源化工有限公司 | D-对羟基苯甘氨酸的制备方法 |
WO2009127446A1 (en) * | 2008-04-17 | 2009-10-22 | Deretil, S.A. | METHOD FOR THE PREPARATION OF D-p-HYDROXYPHENYLGLYCINE |
CN101613298A (zh) * | 2008-06-25 | 2009-12-30 | 河南新天地药业有限公司 | 水相拆分法生产d-(-)-对羟基苯甘氨酸技术 |
CN102603449B (zh) * | 2012-02-15 | 2015-07-15 | 河南新天地药业股份有限公司 | 一种左旋对羟基苯甘氨酸类化合物的合成方法 |
-
2012
- 2012-02-15 US US13/994,085 patent/US8940928B2/en active Active
- 2012-02-15 CA CA2818094A patent/CA2818094C/en active Active
- 2012-02-15 JP JP2013558293A patent/JP5767346B2/ja active Active
- 2012-02-15 WO PCT/CN2012/071159 patent/WO2013120257A1/zh active Application Filing
- 2012-02-15 GB GB1308404.1A patent/GB2503341B/en active Active
- 2012-02-15 MX MX2013006993A patent/MX342892B/es active IP Right Grant
- 2012-02-15 ES ES201390067A patent/ES2429431B2/es active Active
Also Published As
Publication number | Publication date |
---|---|
US8940928B2 (en) | 2015-01-27 |
ES2429431A2 (es) | 2013-11-14 |
ES2429431B2 (es) | 2014-05-30 |
CA2818094C (en) | 2016-11-08 |
GB201308404D0 (en) | 2013-06-19 |
JP5767346B2 (ja) | 2015-08-19 |
JP2014515733A (ja) | 2014-07-03 |
GB2503341B (en) | 2020-04-15 |
GB2503341A (en) | 2013-12-25 |
ES2429431R1 (es) | 2013-12-17 |
US20140350295A1 (en) | 2014-11-27 |
CA2818094A1 (en) | 2013-08-15 |
WO2013120257A1 (zh) | 2013-08-22 |
MX2013006993A (es) | 2013-12-06 |
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