Fluorous tagging and scavenging reactants and methods of...

Chemistry of hydrocarbon compounds – Compound or reaction product mixture – Aromatic

Reexamination Certificate

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C548S542000

Reexamination Certificate

active

07576245

ABSTRACT:
The present invention includes methods and compositions for increasing the fluorous nature of an organic compound by reacting it with at least one fluorous compound to produce a fluorous tagged organic compound. The increased fluorous nature of the fluorous tagged organic compound can then be utilized to separate the fluorous organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom. The resultant fluorous tagged organic compound can be subjected to subsequent chemical transformations, wherein the fluorous nature of the tagged compound is utilized to increase the ease of separation of the fluorous tagged organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom, after each chemical transformation. The chemical transformations result in a second fluorous tagged organic compound wherein the fluorous nature of the second fluorous tagged organic compound can then be reduced by removing the fluorous group therefrom, thereby producing a second organic compound that may be employed as a pharmaceutical compound or intermediate, or a combinatorial library component.

REFERENCES:
patent: 4022897 (1977-05-01), Yale et al.
patent: 4098894 (1978-07-01), Buchel et al.
patent: 4745191 (1988-05-01), Husbands
patent: 5236923 (1993-08-01), Kirsten et al.
patent: 5463082 (1995-10-01), Horvath et al.
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: 6673539 (2004-01-01), Wipf et al.
patent: 6727390 (2004-04-01), Curran et al.
patent: 6734318 (2004-05-01), Curran et al.
patent: 6749756 (2004-06-01), Curran et al.
patent: 6806357 (2004-10-01), Curran et al.
patent: 6825043 (2004-11-01), Curran et al.
patent: 6861544 (2005-03-01), Curran et al.
patent: 6897331 (2005-05-01), Curran et al.
patent: 1925555 (1971-01-01), None
patent: 0 248 697 (1987-12-01), None
patent: 0328111 (1989-08-01), None
patent: 0 354 297 (1990-02-01), None
patent: 0 468 531 (1992-01-01), None
patent: 0628316 (1994-12-01), None
patent: 1143481 (1969-02-01), None
patent: 1269096 (1972-03-01), None
patent: 58-057325 (1983-04-01), None
patent: 62205350 (1987-09-01), None
patent: 62278551 (1987-12-01), None
patent: 63-239254 (1988-10-01), None
patent: 07207021 (1995-08-01), None
patent: WO 97/01562 (1997-01-01), None
patent: WO 98/25916 (1998-06-01), None
patent: WO 00/18774 (2000-04-01), None
patent: WO 01/61332 (2001-08-01), None
Hasegawa et al., 2002, CAS: 138:56214.
Curran, “Strategy-Level Separations in Organic Synthesis: From Planning to Practice,” Angew. Chem., Int. Ed. Eng., (1998) 37, 1175-1196.
Flynn, “Phase-Trafficking Reagents and Phase-Switching Strategies for Parallel Synthesis,” Med. Res. Rev., (1999) 19, 408-431, John Wiley & Sons, Inc.
Kaldor et al., “Combinatorial chemistry using polymer-supported reagents,” Curr. Opin. Chem. Bio., (1997) 1, 101-106.
Shuttleworth et al., “Functionalised Polymers: Recent Developments and New Applications in Synthetic Organic Chemistry,” Synthesis, (1997) 1217-1239.
Ley et al., “Multi-step organic synthesis using solid-supported reagents and scavengers: a new paradigm in chemical library generation,” J. Chem. Soc., Perkin Trans. 1, (2000) 3815-4195.
Eames et al., “Polymeric Scavenger Reagents in Organic Synthesis,” Eur. J. Org. Chem., (2001) 1213-1224.
Danielson et al., “Fluoropolymers and fluorocarbon bonded phases as column packings for liquid chromatography,” J. Chromat., (1991) 544, 187-199, Elsevier Science Publishers B.V.
Curran, “Fluorous Reverse Phase Silica Gel. A New Tool for Preparative Separations in Synthetic Organic and Organofluorine Chemistry,” Synlett, (2001) 9, 1488-1496.
Zhang, “Fluorous Synthesis of Disubstituted Pyrimidines,” Org. Lett., (2003) 5, 1011-1013.
Chen et al., “FluoMar, a Fluorous Version of the Marshall Resin for Solution-Phase Library Synthesis,” Org. Lett., (2003) 5, 1015-1017.
Zhang et al., “Fluorous electrophilic scavengers for solution-phase parallel synthesis,” Tet. Lett., (2003) 44, 2065-2068.
Orain et al., “Protecting Groups in Solid-Phase Organic Synthesis,” J. Combinatorial Chem., (2002) 4, 1-16.
Studer et al., “Fluorous Synthesis: A Fluorous-Phase Strategy for Improving Separation Efficiency in Organic Synthesis,” Science, (1997) 275, 823-826.
Studer et al., “A Strategic Alternative to Solid Phase Synthesis: Preparation of a Small Isoxazoline Library by ‘Fluorous Synthesis’,” Tetrahedron, (1997) 53, 6681-6696.
Studer et al., “Fluorous Synthesis: Fluorous Protocols for the Ugi and Biginelli Multicomponent Condensations,” J. Org. Chem., (1997) 62, 2917-2924.
Curran et al., “Preparation of a Fluorous Benzyl Protecting Group and Its Use in a Fluorous Synthesis Approach to a Disaccharide,” Tet. Lett., (1998) 39, 4937-4940.
Curran et al., “Fluorous Synthesis with Fewer Fluorines (Light Fluorous Synthesis): Separation of Tagged from Untagged Products by Solid-Phase Extraction with Fluorous Reverse-Phase Silica Gel,” J. Am. Chem. Soc., (1999) 121, 9069-9072.
Zhang et al., “Separation of ‘Light Fluorous’ Reagents and Catalysts by Fluorous Solid-Phase Extraction: Synthesis and Study of a Family of Triarylphosphines Bearing Linear and Branched Fluorous Tags,” J. Org. Chem., (2000) 65, 8866-8873.
Luo et al., “Fluorous Boc (F-Boc) Carbamates: New Amine Protecting Groups for Use in Fluorous Synthesis,” J. Org. Chem., (2001) 66, 4261-4266.
Luo et al., “Fluorous Mixture Synthesis: A Fluorous-Tagging Strategy for the Synthesis and Sepration of Mixtures of Organic Compounds,” Science, (2001) 291, 1766-1769.
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 substituent,” Tetrahedron, (2001) 57, 5243-5253.
Chen et al., “‘Analogous’ Organic Synthesis of Small-Compound Libraries: Validation of Combinatorial Chemistry in Small-Molecule Synthesis,” J. Am. Chem. Soc. (1994) 116, 2661-2662.
Bauer et al., “A Novel Linkage for the Solid-Phase Synthesis of Hydroxamic Acids,” Tet. Lett., (1997) 38, 7233-7236.
Matthews et al., “Parallel Synthesis of Alkyl Tetrazole Derivatives Using Solid Support Chemistry,” J. Combinatorial Chem., (2000) 2, 19-23.
Findeis et al., “Nitrobenzophenone Oxime Based Resins for the Solid-Phase Synthesis of Protected Peptide Segments,” J. Org. Chem., (1989) 54, 3478-3482.
Booth et al., “Solid-Supported Reagent Strategies for Rapid Purification of Combinatorial Synthesis Products,” Acc. Chem. Res., (1999) 32, 18-26.
Hodges, “Covalent Scavengers for Primary and Secondary Amines,” Synlett, (1999) 1, 152-158.
Shuttleworth et al., “Functionalised Polymers in Organic Chemistry; Part 2,” Synthesis (2000) 8, 1035-1074.
Linclau et al., “Organic-Fluorous Phase Switches: A Fluorous Amine Scavenger for Purification in Solution Phase Parallel Synthesis,” J. Org. Chem, (1999) 64, 2835-2842.
Zhang et al., “Use of fluorous silica gel to separate fluorous thiol quenching derivatives in solution-phase parallel synthesis,” Tetrahedron, (2002) 58, 3871-3875.
Gooding et al., “Enantioselective Synthesis of 2-Substituted Pyrrolidines From 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist RS-59022,” Synth.. Commun., (1995) 25, 1155-1166.
Booth et al., Polymer-Supported Quenching Reagents for Parallel Purification, J. Am. Chem. Soc., (1997), 119, 4882-4886.
Blackburn et al., “Parallel Synthesis of 3-Aminoimidazo[1,2-a]pyridines and pyrazines by a New Three-Component Condensation,” Tet. Lett., (1998) 39, 3635-3638.
Creswell et al., “Combinatorial Synthesis of Dihydropyridone Libraries and

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