EP1421059A1 - Procede de preparation de derives de n-acyl-beta-amino acides enrichis en enantiomeres par hydrogenation enantioselective de (z)-enamides correspondants - Google Patents

Procede de preparation de derives de n-acyl-beta-amino acides enrichis en enantiomeres par hydrogenation enantioselective de (z)-enamides correspondants

Info

Publication number
EP1421059A1
EP1421059A1 EP02757176A EP02757176A EP1421059A1 EP 1421059 A1 EP1421059 A1 EP 1421059A1 EP 02757176 A EP02757176 A EP 02757176A EP 02757176 A EP02757176 A EP 02757176A EP 1421059 A1 EP1421059 A1 EP 1421059A1
Authority
EP
European Patent Office
Prior art keywords
process according
alkyl
group
atoms
formula
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.)
Withdrawn
Application number
EP02757176A
Other languages
German (de)
English (en)
Inventor
Christophe Guillaume Malan
Christopher Cobley
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.)
Dow Global Technologies LLC
Original Assignee
Dow Global Technologies LLC
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.)
Filing date
Publication date
Application filed by Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Publication of EP1421059A1 publication Critical patent/EP1421059A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • 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
    • C07C233/01—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
    • C07C233/51—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 an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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

L'invention concerne un procédé de préparation d'un dérivé de bêta-amino-acide enrichi en énantiomères représenté par la formule (1), ou l'énantiomère opposé de celui-ci, formule dans laquelle R1 est un groupe alkyle, aryle ou hétéroaryle éventuellement substitué, contenant jusqu'à 20 atomes C, R2 est un groupe alkyle contenant jusqu'à 20 atomes C, et R3 est H ou un groupe alkyle ou aryle contenant jusqu'à 20 atomes C, ledit procédé comprenant l'hydrogénation asymétrique du précurseur (z)-énamide (2) dans un solvant ou cosolvant alcoolisé, catalysé par un complexe de rhodium cationique d'un ligand de phosphine chiral représenté par la formule partielle (3), dans laquelle n est une valeur de 0 à 6 et R représente au moins un groupe organique non hydrogène contenant jusqu'à 20 atomes C.
EP02757176A 2001-08-17 2002-08-16 Procede de preparation de derives de n-acyl-beta-amino acides enrichis en enantiomeres par hydrogenation enantioselective de (z)-enamides correspondants Withdrawn EP1421059A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0120167A GB0120167D0 (en) 2001-08-17 2001-08-17 Asymmetric hydrogenation
GB0120167 2001-08-17
PCT/US2002/026142 WO2003016264A1 (fr) 2001-08-17 2002-08-16 Procede de preparation de derives de n-acyl-beta-amino acides enrichis en enantiomeres par hydrogenation enantioselective de (z)-enamides correspondants

Publications (1)

Publication Number Publication Date
EP1421059A1 true EP1421059A1 (fr) 2004-05-26

Family

ID=9920631

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02757176A Withdrawn EP1421059A1 (fr) 2001-08-17 2002-08-16 Procede de preparation de derives de n-acyl-beta-amino acides enrichis en enantiomeres par hydrogenation enantioselective de (z)-enamides correspondants

Country Status (4)

Country Link
EP (1) EP1421059A1 (fr)
JP (1) JP2005518339A (fr)
GB (1) GB0120167D0 (fr)
WO (1) WO2003016264A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR043515A1 (es) * 2003-03-19 2005-08-03 Merck & Co Inc Procedimiento para preparar derivados quirales beta aminoacidos mediante hidrogenacion asimetrica
CN1579627A (zh) * 2003-08-05 2005-02-16 中国科学院大连化学物理研究所 一种手性配体金属络合物催化体系及制法和应用
DE102005014054A1 (de) * 2005-03-23 2006-09-28 Degussa Ag Elektronenarme Bisphospholanliganden und -katalysatoren
WO2011146610A2 (fr) * 2010-05-19 2011-11-24 Dr. Reddy's Laboratories Ltd. Synthèse énantiosélective d'amines chirales pour la production de rotigotine
MX2012014574A (es) 2010-06-15 2013-02-07 Bayer Ip Gmbh Derivados diamidoantranilicos que tienen cadenas laterales ciclicas.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG42936A1 (en) * 1992-04-02 1997-10-17 Ciba Geigy Ag Ferrocenyl diphosphines as ligands for homogeneous catalysts
JP3493206B2 (ja) * 1993-03-19 2004-02-03 ダイセル化学工業株式会社 光学活性β−アミノ酸類の製法
DE10100971A1 (de) * 2001-01-11 2002-07-18 Degussa Verfahren zur Herstellung enantiomerenangereicherter beta-Aminosäure

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03016264A1 *

Also Published As

Publication number Publication date
WO2003016264A1 (fr) 2003-02-27
JP2005518339A (ja) 2005-06-23
GB0120167D0 (en) 2001-10-10

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