Removal of ruthenium by-product by supercritical fluid...

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Cyclic peptides

Reexamination Certificate

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C556S021000, C556S022000, C548S101000, C540S460000, C034S329000, C034S337000, C570S190000, C570S211000

Reexamination Certificate

active

11006475

ABSTRACT:
A process for removing ruthenium or ruthenium-containing compounds from a reaction mixture comprising a compound of the following formula I in an organic solvent using supercritical fluid processing techniques:wherein RA, R3, R4, D and A are as defined herein. This invention has particular application for removing ruthenium-containing catalyst and ruthenium-containing catalyst by products from reaction mixtures that result from ring-closing olefin metathesis (RCM) reactions.

REFERENCES:
patent: 5811515 (1998-09-01), Grubbs et al.
patent: 5840820 (1998-11-01), DeSimone et al.
patent: 6306987 (2001-10-01), Van Der Schaaf et al.
patent: 6323180 (2001-11-01), Llinas-Brunet et al.
patent: 6608027 (2003-08-01), Tsantrizos et al.
patent: 7148347 (2006-12-01), Brandenburg et al.
patent: 2003/0181363 (2003-09-01), Llinas-Brunet et al.
patent: 2003/0224977 (2003-12-01), Llinas-Brunet et al.
patent: 2004/0248779 (2004-12-01), Dersch et al.
patent: 2005/0049187 (2005-03-01), Bradenburg et al.
patent: 2005/0075279 (2005-04-01), Llinas et al.
patent: 2005/0080005 (2005-04-01), Llinas-Brunet et al.
patent: 2005/0119453 (2005-06-01), Brenner et al.
patent: 2005/0215423 (2005-09-01), Brenner et al.
patent: 2006/0063915 (2006-03-01), Gallou et al.
patent: 0009543 (2000-02-01), None
patent: 0009558 (2000-02-01), None
patent: WO 02/081414 (2002-10-01), None
patent: 2004089974 (2004-10-01), None
patent: 2004092203 (2004-10-01), None
Fuerstner, Alois, et al; Olefin Metathesis in Compressed Carbon Dioxide, Angew Chem. Int. Ed. Engl. 1997, 36 No. 22—XP 002102059.
U.S. Application entitled Ring-Closing Metathesis Process in Supercritical Fluid, filed Sep. 9, 2005 and accorded U.S. Appl. No. 11/222,882.
W. Leitner, Homogeneous catalysts for application in supercritical carbon dioxide as a ‘green’ solvent; C.R. Acad. Sci. Paris, Serie llc, Chimie/ Chemistry 3 (2000), 595-600.
Furstner, A., Olefinmetathese in Komprimiertem Kohlendioxid; Angew. Chem., 1997, 109, 2562.
Furstner, A., et al., Olefin Metathesis in Supercritical Carbon Dioxide; J. Amer. Chem. Soc., 2001, 123, 9000-9006.
Grubbs and Chang; Recent Advances in Olefin Metathesis and Its Application in Organic Sythesis; Tetrahedron report number 448; vol. 54; 1998; pp. 4413-4450; Elsevier Science Ltd.
Fuerstner; Olefin Metathesis and Beyond; Angewandte Chemie Int. Ed.; 2000; vol. 39; pp. 3012-3043.
Maynard and Grubbs; Purification Technique for the Removal of Ruthenium from Olefin Metathesis Reaction Products; Tetrahedron Letters; vol. 40; 1999; pp. 4137-4140; Elsevier Science Ltd.
Paquette, et al; A Convenient Method for Removing All Highly-Colored Byproducts Generated during Olefin Metathesis Reactions; Organic Letters; vol. 2, No. 9; 2000; pp. 1259-1261.
Ahn, et al; A Convenient Method for the Efficient Removal of Rithenium Byproducts Generated during Olefin Metathesis Reactions; Organic Letters; vol. 3, No. 9; 2001; pp. 1411-1413.
Cho, et al; An Efficient Method for Removal of Ruthenium Byproducts from Olefin Metathesis Reactions; Organic Letters; vol. 5, No. 4; 2003; pp. 531-533.
Jafarpour, et al; Preparation and Activity of Recyclable Polymer-Supported Ruthenium Olefin Metathesis Catalysts; Organometallics; vol. 21; 2002; pp. 671-679.
Jafarpour, et al; Indenylidenep-Imidazolylidene Complexes of Ruthenium as Ring-Closing Metathesis Catalysts; Organometallics; vol. 18; 1999; pp. 5416-5419.
Dias and Grubbs; Synthesis and Investigation of Homo- and Heterobimetallic Ruthenium Olefin Metathesis Catalysts Exhibiting Increased Activities; Organometallics; vol. 17; 1998; pp. 2758-1767.
Sanford, et al; Mechanism and Activity of Ruthenium Olefin Metathesis Catalysts; Journal of American Chemical Society; vol. 123; 2001; pp. 6543-6554.
Kingsbury, et al; A Recyclable Ru-Based Metathesis Catalyst; Journal of American Chemical Society; vol. 121; 1999; pp. 791-799.
Huang, et al; Olefin Metathesis-Active Ruthenium Complexes Bearing a Nucleophilic Carbene Ligand; Journal of American Chemical Society; vol. 121; 1999; pp. 2674-2678.
Van Veldhuizen, et al; A Recyclable Chiral Ru Catalyst for Enantioselective Olefin Metathesis. Efficient Catalytic Asymmetric Ring-Opening/Cross Metathesis in Air; Journal of American Chemical Society; vol. 124; 2002; pp. 4954-4955.
Men, et al; Substrate Synthesis and Activity Assay for MurG; Journal of American Chemical Society; vol. 120; 1998; pp. 2484-2485.
Dias, et al; Well-Defined Ruthenium Olefin Metathesis Catalysts: Mechanism and Activity; Journal of American Chemical Society; vol. 119; 1997; pp. 3887-3897.
Schwab; Synthesis and Applications of RUC12(=CHR')(PRe)2: The Influence of the Alkylidene Moiety of Metathesis Activity; Journal of American Chemical Society; vol. 118; 1996; pp. 100-110.
Miller, et al; Application of Ring-Closing Metathesis to the Sythesis of Ridified Amino Acids and Peptides; Journal of American Chemical Society; vol. 118; 1996; pp. 9606-9614.
Fu and Grubbs; The Application of Catalytic Ring-Closing Olefin Metathesis to the Synthesis of Unsaturated Oxygen Heterocycles; Journal of American Chemical Society; vol. 114; 1992; pp. 5426-5427.
Kirkland, et al; Ring-Closing Metathesis in Methanol and Water; Journal of Organic Chemistry; vol. 63; 1998; pp. 9904-9909.
Ulman and Grubbs; Ruthenium Carbene-Based Olefin-Metathesis Initiators: Catalyst Decomposition and Longevity; Journal of Organic Chemistry; vol. 64; 1999; pp. 7202-7207.
Hinderling, et al; Olefin Metathesis of a Ruthenium Carbene Complex by Electrospray Ionization in the Gas Phase; Angewandte Chemie International Edition; vol. 37; No. 19; 1998; pp. 2685-2689.
Grissom and Huang; Low-Temperature Tandem Enyne Allene Radical Cyclizations: Efficient Synthesis of 2,3-Dihydroindenes from Simple Enediynes; Angewandte Chemie International Edition; vol. 34; No. 18; 1995; pp. 2037-2039.
Grela, et al; A Highly Efficient Ruthenium Catalyst for Metathesis Reactions; Angewandte Chemie International Edition; vol. 41; No. 21; 2002; pp. 4038-4040.
Rano and Chapman; Solid Phase Synthesis of Aryl Ethers Via the Mitsunobu Reaction; Tetrahedron letters; vol. 36, No. 22; 1995; pp. 3789-3792.
Krchnak, et al; Polymer-Supported Mitsunobu Ether Formation and its Use in Combinatorial Chemistry; Tetrahedron Letters; vol. 36, No. 35; 1995; pp. 6193-6196.
Mitsunobu; The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products; Synthesis; 1981; pp. 1-28; published by Georg Thieme Verlag; Stuttgart and New York.

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