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Title:
DYNAMIC RESOLUTION OF ISOMERS AND RESOLVED ISOMERS
Document Type and Number:
WIPO Patent Application WO2002028809
Kind Code:
A3
Abstract:
Provided is a dynamic resolution method of enriching a desired isomer of an alpha-substituted carboxylic acid relative to an undesired isomer, the method comprising: (a) in a solvent, contacting the alpha-substituted carboxylic acid, wherein the alpha substitution is with a leaving group and wherein the alpha carbon is chiral, with a homochiral amine to form a salt that is partially insoluble under selected reaction conditions, wherein the homochiral amine is selected so that the solubility of the amine salt of the undesired alpha-substituted carboxylic acid is greater than that of the amine salt of the desired alpha-substituted carboxylic acid under the selected reaction conditions; (b) reacting under the selected reaction conditions the salt with a nucleophile, wherein the reacting is effective in producing a net increase in the less soluble amine salt of the alpha-substituted carboxylic acid, and wherein the selected conditions are selected to (i) promote nucleophilic substitution of the nucleophile and the leaving group or (ii) to produce the increase in the less soluble amine salt in the absence of a strong base; and (c) maintaining the reaction for a period of time effective to increase the amount of the desired alpha-substituted carboxylic acid isomer.

Inventors:
VENIT JOHN J (US)
MADDING GARY D (US)
ROSSO VICTOR W (US)
OKUNIEWICZ FRANCIS J (US)
DISCORDIA ROBERT P (US)
KIAU SUSANNE (US)
KOTNIS ATUL S (US)
RANDAZZO MICHAEL E (US)
HENNINGS DAVID D (US)
ZHU JINGYANG (US)
CHEN JASON G (US)
Application Number:
US0129783W
Publication Date:
June 27, 2002
Filing Date:
September 24, 2001
Export Citation:
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Assignee:
BRISTOL-MYERS SQUIBB COMPANY
VENIT, JOHN, J.
MADDING, GARY, D.
ROSSO, VICTOR, W.
OKUNIEWICZ, FRANCIS, J.
DISCORDIA, ROBERT, P.
KIAU, SUSANNE
KOTNIS, ATUL, S.
RANDAZZO, MICHAEL, E.
HENNINGS, DAVID, D.
ZHU, JINGYANG
CHEN, JASON, G.
International Classes:
C07B57/00; C07C51/41; C07C51/43; C07C51/487; C07C57/58; C07C213/08; C07C213/10; C07C327/32; C07D233/74; C07D233/78; C07K1/06; C07K5/062; (IPC1-7): C07C213/08; C07C51/41; C07C51/43; C07C213/10; C07D233/78; C07K5/06
Domestic Patent References:
WO2000024923A12000-05-04
Foreign References:
EP0599444A11994-06-01
Other References:
CAMPS, PELAYO, PÉREZ; FRANCESC; SOLDEVILLA, NURIA: "(R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrr olidonone as chiral auxiliaries for the asymmetric synthesis of alpha-hydroxy acids" TETRAHEDRON: ASYMMETRY, vol. 8, no. 11, 1997, pages 1877-1894, XP002191169
TOLMAN, VLADIMIR; SEDMERA, PETR: "Chemistry of 4-fluoroglutamic acid. Part 3. Preparation of diastereomers of 4-fluoroglutamine and 4-fluoroisoglutamine. An enzamatic access to the antipodes of 4-amino-2-fluorobutyric acid" JOURNAL OF FLUORINE CHEMISTRY, vol. 101, no. 1, - 2000 pages 5-10, XP002191170
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