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1. WO2004020429 - KINETIC RESOLUTION METHOD

Publication Number WO/2004/020429
Publication Date 11.03.2004
International Application No. PCT/US2002/027283
International Filing Date 27.08.2002
Chapter 2 Demand Filed 20.03.2003
IPC
C07C 27/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
27Processes involving the simultaneous production of more than one class of oxygen-containing compounds
C07C 29/10 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
29Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
09by hydrolysis
10of ethers, including cyclic ethers, e.g. oxiranes
C07D 301/32 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
301Preparation of oxiranes
32Separation; Purification
C07D 303/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
303Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02Compounds containing oxirane rings
04containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
C07D 303/08 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
303Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02Compounds containing oxirane rings
08with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
C07D 303/48 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
303Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
02Compounds containing oxirane rings
48with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
CPC
C07B 2200/07
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
2200Indexing scheme relating to specific properties of organic compounds
07Optical isomers
C07C 2523/75
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
2523Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
70of the iron group metals or copper
74Iron group metals
75Cobalt
C07C 27/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
27Processes involving the simultaneous production of more than one class of oxygen-containing compounds
C07C 29/106
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
CACYCLIC OR CARBOCYCLIC COMPOUNDS
29Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
09by hydrolysis
10of ethers, including cyclic ethers, e.g. oxiranes
103of cyclic ethers
106of oxiranes
C07D 301/32
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
301Preparation of oxiranes
32Separation; Purification
C07D 303/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
303Compounds containing three-membered rings having one oxygen atom as the only ring heteroatom
02Compounds containing oxirane rings
04containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Applicants
  • RHODIA PHARMA SOLUTIONS INC. [US]/[US]
Inventors
  • LARROW, Jay, F.
  • JASMIN, Serge
  • LIU, Yi
  • DI MARE, Marcello
Agents
  • McVEIGH, Kevin, E.
Priority Data
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) KINETIC RESOLUTION METHOD
(FR) PROCEDE DE RESOLUTION CINETIQUE
Abstract
(EN)
A method for stereoselective chemical synthesis, includes the steps of: (A) reacting a nucleophile and a chiral or prochiral cyclic substrate, said substrate comprising a carbocycle or a heterocycle having a reactive center susceptible to nucleophilic attack by the nucleophile, in the presence of a chiral non-racemic catalyst to produce a product mixture comprising a stereoisomerically enriched product wherein the product mixture further comprises a catalyst residue, at least a portion of the catalyst residue is in a first oxidation state, and the catalyst residue in the first oxidation state is active in catalyzing degradation of the stereoisomerically enriched product, and (B) chemically or electrochemically changing the oxidation state of the catalyst residue form the first oxidation state to a second oxidation state, wherein catalyst residue in the second oxidation state is less active in catalyzing degradation of the stereoisomerically enriched product than is catalyst residue in the first oxidation state. The method reduces erosion of the chiral purity of the stereoisomerically enriched product and reduces the chemical transformation to side products of the stereoisomerically enriched product and co-product(s). The deactivated catalyst is recoverable and recyclable.
(FR)
Un procédé de synthèse chimique stéréosélective consiste en ce qui suit: (A) faire réagir un nucléophile et un substrat cyclique chiral ou prochiral, ledit substrat comprenant un carbocycle ou un hétérocycle possédant un centre réactif vulnérable aux attaques nucléophiliques par le nucléophile, en présence d'un catalyseur chiral non racémique, pour produire un mélange de produits comprenant un produit enrichi stéréoisomériquement, le mélange de produits comprenant également un résidu de catalyseur dans le premier état d'oxydation, au moins une partie du résidu de catalyseur se trouvant dans un premier état d'oxydation, et le résidu de catalyseur dans le premier état d'oxydation étant actif en termes de dégradation catalytique du produit enrichi stéréoisomériquement; et (B) modifier par procédé chimique ou électrochimique l'état d'oxydation du résidu de catalyseur, qui passe du premier état d'oxydation à un deuxième état d'oxydation, le résidu de catalyseur dans le deuxième état d'oxydation étant moins actif en termes de dégradation catalytique du produit enrichi stéréoisomériquement que le résidu de catalyseur dans le premier état d'oxydation. Le procédé réduit l'érosion de la pureté chirale du produit enrichi stéréoisomériquement et la transformation chimique des produits secondaires du produits et des coproduits enrichi stéréoisomériquement. Le catalyseur désactivé peut être récupéré et recyclé.
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