Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Reexamination Certificate
2007-05-08
2007-05-08
Barts, Samuel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
Reexamination Certificate
active
10442664
ABSTRACT:
A method of obtaining an enantioenriched organic compound comprising the steps of: 1) generating from a starting racemic, non-enantiopure or achiral compound a first mixture comprising at least one fluorous-tagged compound and at least one other non-fluorous tagged compound, at least one of these two compounds being enantioenriched relative to the starting compound; 2) contacting a first non-fluorous phase including the first mixture with a fluorous phase at a first phase interface, the fluorous-tagged compound distributing between the first non-fluorous phase and the fluorous phase; and 3) contacting the fluorous phase with a second non-fluorous phase at a second phase interface. The method further includes the step of having a third compound in the second non-fluorous phase that reacts with the fluorous-tagged compound to produce a second compound and the step of generating the first mixture by chemical or enzymatic kinetic resolution of a racemic or non-enantiopure compound.
REFERENCES:
patent: 5777121 (1998-07-01), Curran et al.
patent: 5859247 (1999-01-01), Curran et al.
patent: 6156896 (2000-12-01), Curran et al.
patent: 2003/0003552 (2003-01-01), Theil et al.
patent: 2003/0148481 (2003-08-01), Theil et al.
patent: 19963314 (2001-06-01), None
patent: 19963315 (2001-06-01), None
patent: 1321528 (2003-07-01), None
“Resolution of 1-(2-Naphthyl)ethanol by a Combination of an Enzyme-Catalyzed Kinetic Resolution with a Fluorous Triphasic Separative Reaction” Organic Letters (2002), 4(15), 2585-2587, Luo et al.
Dennis P. Curran, Strategy-Level Separations in Organic Synthesis: From Planning to Practice, Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
Armido Studer et al., Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis, Science, vol. 275, Feb. 7, 1997, 823-826.
Armido Studer et al., A Strategic Alternative to Solid Phase Synthesis: Preparation of a Small Isoxazoline Library by “Fluorous Synthesis”, Tetrahedron, vol. 53, No. 19, 6681-6696, 1997.
Zhiyong Luo et al., Fluorous Mixture Synthesis: A Fluorous-Tagging Strategy for the Synthesis and Separation of Mixtures of Organic Compounds, Science, vol. 291, Mar. 2, 2001, 1766-1769.
Hiroyuki Nakamura et al., Fluorous Triphasic Reactions: Transportative Deprotection of Fluorous Silyl Ethers with Concomitant Purification, J. Am. Chem. Soc. 2001, 123, 10119-10120.
Dennis P. Curran et al., Thiol additions to acrylates by Fluorous mixture synthesis: relative control of elution order in demixing by the Fluorous tag and the thiol substitutent, Tetrahedron 57, 2001, 5243-5253.
Dennis P. Curran et al., “Experimental techniques in Fluorous synthesis: a user's guide,” in Combinatorial Chemistry: A Practical Approach, Oxford University Press, Oxford, 2001, 327-352.
Andre Collet, Resolution of Racemates: Did You Say “Classical”?, Angew, Chem. Int. Ed. 1998, 37, No. 23, 3239-3241.
Istvan T. Horvath, Fluorous Biphase Chemistry, Acc. Chem. Res., 1998, 31, 641-650.
Luis P. Barthel-Rosa et al., Chemistry in Fluorous media: a user's guide to practical considerations in the application of Fluorous catalysts and reagents, Coordination Chemistry Reviews, 190-192 (1999) 587-605.
Jason Eames, Parallel Kinetic Resolutions, Angew, Chem. Int. Ed., 2000, 39, No. 5, 885-888.
Rolf D. Schmid et al., Lipases: Interfacial Enzymes with Attractive Applications, Angew. Chem. Int. Ed., 1998, 37, 1608-1633.
Stanley M. Roberts, Preparative biotransformations: the employment of enzymes and whole-cells in synthetic organic chemistry, J. Chem. Soc., Perkin Trans. 1, 1998, 157-169.
Peter Somfai, Nonenzymatic Kinetic Resolution of Secondary Alcohols, Angew. Chem. Int. Ed. Engl., 1997, 36, No. 24, 2731-2733.
Yun Oliver Long et al., Non-enzymatic Kinetic Resolution of Racemic Alcohols with Chiral Catalysts, Chemtracts-Organic Chemistry, 13:1-8 (2000).
Stanley M. Roberts, Preparative biotransformations, J. Chem. Soc., Perkin Trans., 1, 2000, 611-633.
Benno Hungerhoff et al., Separation of Enantiomers by Extraction Based on Lipase-Catalyzed Enantiomer-Selective Fluorous-Phase Labeling, Angew. Chem. Int. Ed., 2001, 40, No. 13, 2492-2494.
Dennis P. Curran, “Fluorous Techniques for the Synthesis of Organic Molecules: A Unified Strategy for Reaction and Separation,” In Stimulating Concepts in Chemistry, Shibasaki, Fraser-Stoddart, Vogtle, eds. Wiley-VCH, New York, 2000, 25-37.
J. N. Murrell et al., Properties of liquids and solutions, Wiley, New York, 1982, 1-3.
Jean Jacques et al., Enantiomers, Racemates, and Resolutions, John Wiley & Sons, New York, 1981,252-405.
Eliel, E. L. et al., Racemization, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994, 297-425.
J. A. Gladysz, Are Teflon “Ponytails” the Coming Fashion for Catalysts?, Science, vol. 266, Oct. 7, 1994, 55-56.
Istvan T. Horvath et al., Facile Catalyst Separation Without Water: Fluorous Biphase Hydroformylation of Olefins, Science, vol. 266, Oct. 7, 1994, 72-75.
Dong-Wei Zhu, A Novel Reaction Medium: Perfluorocarbon Fluids, Synthesis, 953-954, 1993.
Gert E. Berendsen et al., (Heptadecafluorodecyl)dimethylsilyl Bonded Phase for Reversed-Phase Liquid Chromatography, Anal. Chem., 1980, 52, 1990-1993.
Hugo A. H. Billiet et al., Retention and Selectivity Characteristics of a Non-Polar Perfluorinated Stationary Phase for Liquid Chromatography, Journal of Chromatography, 218 (1981) 443-454.
M. Hudlicky, Chemistry of Organic Fluorine Compounds, 2 ed., Ellis Horwood Ltd, West Sussex, England, 1992, 542-545.
B. Boutevin et al., Study of the alkylation of chlorosilanes. Part I. Synthesis of tetra(1H,1H,2H,2H-polyfluoralkyl)silanes, Journal of Fluorine Chemistry, 60 (1993) 211-223.
Curran et al., U.S. Appl. No. 09/506,779, filed Feb. 18, 2000.
Curran et al., U.S. Appl. No. 09/877,944, filed Jun. 8, 2001.
Curran et al., U.S. Appl. No. 10/094,345, filed Mar. 8, 2002.
Curran Dennis Patrick
Luo Zhiyong
Barts Samuel
Fluorous Technologies, Inc.
Kirkpatrick & Lockhart Preston Gates & Ellis LLP
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