Multicomponent synthesis of amino acids and derivatives thereof

Details Multicomponent synthesis of amino acids and derivatives thereof Multicomponent synthesis of amino acids and derivatives thereof

2005-08-16

2005-08-16

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C560S019000, C560S038000, C560S039000, C560S040000, C560S045000, C560S046000, C560S047000, C546S190000, C549S013000, C549S356000, C549S551000

Reexamination Certificate

active

06930200

ABSTRACT:
Mono-substituted and di-substituted alpha-amino acids and derivatives thereof, substituted at the alpha positon with one (mono-) or two (di-) substituents (R2and/or R3) as shown in Formula 1: N(R4R5)C(R2R3)CO(OR1).

REFERENCES:
patent: 3489751 (1970-01-01), Crast, Jr.
patent: 3634418 (1972-01-01), Willner
patent: 4535167 (1985-08-01), Freidinger
patent: 4631211 (1986-12-01), Houghten
patent: 4757153 (1988-07-01), Hansen, Jr. et al.
patent: 5280093 (1994-01-01), Jacquier et al.
patent: 726 386 (1942-10-01), None
patent: 36 24 376 (1988-01-01), None
patent: 0 779 076 (1997-06-01), None
patent: 867 572 (1961-05-01), None
Ugi, I. et al “MCR 6:Chiral 2,6-piperazinediones via Ugi reactions . . . ” Heterocycles (1998) vol. 47, No. 2, pp 965-975.
Stryer, Lubert, “Biochemie”, 1983, Vieweg and Sohn Verlagsgesellschaft MBH, Germany XP002221913, pp. 10-14; in particular table 2-1.
Signma-Aldrich Chemie GMBH, “Biochemical and reagents for life science research”, 1999, Sigma-Aldrich Co. XP002221914, pp. 90-95.
Supplementary Partial European Search Report for Application EP 00 90 8331 mailed Jan. 9, 2003.
Cao, X. et al., “Synthesis of NH-acyl-α-aminoamides on rink resin: inhibitors of the hematopoietic protein tyrosine phosphatase” Bioorg. Med. Chem. Lett. vol. 5, 1995, 2953-2958.
Demharter, A. et al. Synthesis of Chiral 1,1′—Iminodicarboxylic Acid Derivatives from—α Amino Acids Aldehydes, Isocyanides, and Alcohols by the Diastereoselective Five-Center-Four-Component Reactron. Angew. Chem. Int. Ed. Engl. 35: 173-175 (1996).
Faust, “Geminal Benzotriazolyl Ethoxy derivatives-Efficient auxiliaries in the synthesis of unsaturated carbonyl compounds”, J. Prakt. Chem., 1997, vol. 339, p. 98-100.
Keating, et al., “Molecular diversity via a convertible isocyanide in the Ugi four component condensation” J. Am. Chem. Soc. 1995, vol. 117, 7842-7843.
Keating, T.A. et al. “Postcondensation Modifications of Ugi Four-Component Products: 1-Isocyanocyclohexene as a convertible Isocyanide Mechanism of Conversion, Synthesis of Diverse Structures, and Demonstration of Resin Capture” J. Am. Chem. Soc. 1996, vol. 118, p 2574-2583.
Kitaguchi et al.“Enzymatic formation of an isopeptide bond involving the E-amino group of lysine” Tetrahedron Lett., 1988, vol. 29, pp. 5487-5488.
Kunz, H. et al. “Carbohydrates as chiral templates: diastereoselective Ugi synthesis of (S) amino acids using o-acylated d-arabinopyranosylamine as the auxiliary” Tetrahedron . Lett., 1989, vol. 30, pp. 4109-4110.
Linderman, “Enhanced diastereoselectivity in the asymmetric Ugi reaction using a new convertible isonitrile” J. Org. Chem., 1999, vol. 64, pp. 336-337.
Mjalli, et al., “Solid phase synthesis of pyrroles derived from a four component condensation” Tetrahedron Lett., 1996, vol. 37, pp. 2943-2946.
Siglmüller et al. “Chiral ferrocenylalkylamines from (−)-menthone” Tetrahedron, 1986, vol. 42, pp. 5931-5940.
Ugi, I., Isonitrile Chemistry, p. 1, Academic Press, New York and London, 1971.
Ugi, I., “From Isocyanides via four-component condensations to antibiotic synthesis” Angew Chem., Int. Ed. Engl., 1982, vol. 21, pp. 810-819.
Ugi, I., “Perspektiven von Multikomponentenreaktionen und deren Bibliotheken” J. Prakt. Chem., 1997, vol. 339, p. 499-516.
Ugi et al., “Die Kondensation von Carbonsauren, Aldehyden und Isonitrilen mit primaren aliphatischen Aminen, die einen abspaltbaren Alkyl-oder Alkenyl-Rest tragen” Chem. Ber., vol. 97, pp. 2996-3005 (1964).
Dömling et al. “Multicomponent Reactions with Isocyanides”Angew. Chem. Int. Ed.,vol. 39, pp. 3168-3210 (2000).

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