Synthesis of 2-alkyl amino acids

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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C560S012000, C560S019000

Reexamination Certificate

active

07038073

ABSTRACT:
A method of preparing a 2-alkyl amino acid involves the aziridination of an alkylacrylate and the opening of the aziridine ring by addition of a side chain. This method can result in the preparation of enantiomeric excess of a 2-alkyl amino acid. The invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. In this method, an aryl nitrile or imidate is condensed with cysteine, a 2-alkyl cysteine, or a cysteine ester.

REFERENCES:
patent: 4406905 (1983-09-01), Zähner et al.
patent: 5554753 (1996-09-01), O'Donnell et al.
patent: 5840739 (1998-11-01), Bergeron, Jr.
patent: 5872259 (1999-02-01), Reuter
patent: 5929232 (1999-07-01), Jacobsen et al.
patent: 5929252 (1999-07-01), Sharpless et al.
patent: 6083966 (2000-07-01), Bergeron, Jr.
patent: 6159983 (2000-12-01), Bergeron, Jr.
patent: 6383233 (2002-05-01), Reuter
patent: 6428583 (2002-08-01), Reuter
patent: 6521652 (2003-02-01), Bergeron
patent: 6525080 (2003-02-01), Bergeron
patent: 6559315 (2003-05-01), Bergeron
patent: 2003/0088105 (2003-05-01), Krich et al.
patent: 2003/0220504 (2003-11-01), Chorghade et al.
patent: 2003/0225287 (2003-12-01), Chorghade et al.
patent: 2003/0229231 (2003-12-01), Chorghade et al.
patent: 2003/0236404 (2003-12-01), Gimi et al.
patent: 2003/0236426 (2003-12-01), Chorghade et al.
patent: 2003/0236434 (2003-12-01), Gimi et al.
patent: 2003/0236435 (2003-12-01), Gimi et al.
patent: 2004/0002613 (2004-01-01), Chorghade et al.
patent: 2004/0024224 (2004-02-01), Chorghade et al.
patent: 20 20 866 (1971-11-01), None
patent: 30 02 989 (1981-07-01), None
patent: 1 302 467 (2003-04-01), None
patent: 1 292 170 (1972-10-01), None
patent: WO 94/11367 (1994-05-01), None
patent: WO 97/36885 (1997-10-01), None
patent: WO 00/01670 (2000-01-01), None
patent: WO 00/12493 (2000-03-01), None
patent: WO 00/16763 (2000-03-01), None
Larsson et al., Acta Chemica Scandinavica, 1994, 48(6), pp. 511-516.
Baldwin et al., Tetrahedron, 1993, 49:6309-6330.
Baldwin et al., Journal of the Chemical Society, Chemical Communication, 1989, 23:1852-1854.
Kogami et al., Bulletin of the Chemical Society of Japan, 1987, 60(8):2963-2965.
Evans, D.A., et al., “Development of the Copper-Catalyzed Olefin Aziridination Reaction,”J. Am. Chem. Soc., 116:2742-2753 (1994).
Evans, D.A., et al., “Bis(oxazoline)-Copper Complexes as Chiral Catalysts for the Enantioselective Aziridination of Olefins,”J. Am. Chem. Soc., 115:5328-5329 (1993).
Johnson, J. S., et al., “Chiral Bis(oxazoline) Copper (II) Complexes: Versatile Catalysts for Enantioselective Cycloaddition, Aldol, Michael, and Carbonyl Ene Reactions,”Acc. Chem. Res., 33:325-335 (2000).
Langham, C., et al., “Heterogeneous aziridination of alkenes using Cu2+exchanged zeolites,”Applied Catalysis A: General, 182:85-89 (1999).
Langham, C., et al., “Catalytic asymmetric heterogeneous aziridination of alkenes using zeolite CuHY with [N-(p-tolylsulfony)imino]phenyliodinane as nitrene donor,”J. Chem. Soc., Perkin Trans. 2:1043-1049 (1999).
Langham, C., et al., “Catalytic heterogeneous aziridination of alkenes using microporous materials,”Chem. Commun., 1601-1602 (1998).
Gullick, J., et al., “Aziridination of styrene: comparison of [N-(p-tolylsulfonyl)imino]phenyliodinane and chloramine-T as nitrene donors,”Journal of Molecular Catalysts A: Chemical, 180:85-89 (2002).
Gullick, J., et al., “Heterogeneous catalytic aziridination of styrene using transition-metal-exchanged zeolite Y,”Catalysis Letters, 75(3-4):151-154 (2001).
Taylor, S., “Catalytic asymmetric heterogeneous aziridination of styrene using CuHY: effect of nitrene donor on enantioselectivity,”J. Chem. Soc., Perkin Trans., 2:1714-1723 (2001).
Fuji, K., et al., “A New Access to Chiral Aziridines by Enzymatic Transesterification ofMeso-Bis(Acetoxymethyl)Aziridines,”Tetrahedron Letters, 31(46):6663-6666 (1990).
Ittah, Y., et al., “A New Aziridine Synthesis from 2-Azido Alcohols and Tertiary Phosphines. Preparation of Phenanthrene 9, 10-Imine,”J. Org. Chem., 43(22):4271-4273 (1978).
Konsler, R. G., et al., “Cooperative Asymmetric Catalysis with Dimeric Salen Complexes,”J. Am. Chem. Soc., 120:10780-10781 (1998).
Annis, D. A., et al., “Polymer-Supported Chiral Co(Salen) Complexes: Synthetic Applications and Mechanistic Investigations in the Hydrolytic Kinetic Resolution of Terminal Epoxides,”J. Am. Chem. Soc., 121:4147-4154 (1999).
Senanayake, C. H. and Jacobsen, E. N., “Chiral (Salen)Mn(III) Complexes in Asymmetric Epoxidations: Practical Synthesis of cis-Aminoindanol and Its Application to Enantiopure Drug Synthesis,” in Process Chemistry in the Pharmaceutical Industry, Gadamasetti, K. G., Ed., Dekker: New York, 1999, pp. 347-368.
Myers, J. K., et al., “Asymmetric Synthesis of β-Amino Acid Derivatives via Catalytic Conjugate Addition of Hydrazolic Acid to Unsaturated Imides,”J. Am. Chem. Soc., 121:8959-8960 (1999).
Jacobsen, E. N. and Wu, M. H., “Ring Opening of Epoxides and Related Reactions,” in Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A. and Yamamoto, H., Eds., Springer: New York, 1999, pp. 1309-1326.
Jacobsen, E. N., “Aziridination,” in Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A. and Yamamoto, H., Eds., Springer: New York, 1999, pp. 607-618.
Jacobsen, E. N., “Future Perspectives in Asymmetric Catalysis,” in Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A. and Yamamoto, H., Eds., Springer: New York, 1999, pp. 1473-1477.
Li, Z., et al., “Enantioselective Ring Opening of Meso Aziridines Catalyzed by Tridentate Schiff Base Chromium(III) Complexes,”Organic Letters, 1(10):1611-1613 (1999).
Schaus, S. E., et al., “Asymmetric Ring Opening of Meso Epoxides with TMSCN Catalyzed by (pybox)Ianthanide Complexes,”Organic Letters, 2(7):1001-1004 (2000).
Brandes, B. D., Regioselective Ring Opening of Enantiomerically Enriched Epoxides via Catalysis with Chiral (Salen)Cr(III) Complexes,Synlett, 1013-1015 (2001).
Gurjar, M. K., “Kinetic Resolution of Aryl Glycidyl Ethers: A Practical Synthesis of Optically Pure β-Blocker—S-Metoprolol,”Heterocycles, 48(7):1471-1476 (1998).
Gurjar, M. K., “A Practical Synthesis of (R)-(-)-Phenylephrine Hydrochloride,”Organic Process Research&Development, 2:422-424 (1998).
Chorghade, M.S., et al., “Synthesis of (2S,5S)-trans-S-(4-fluorophenoxymethyl)-2-(1-N-hydroxy ureidyl-3-butyn-4-yl)-tetrahydrofuran-(CMI-977),”Pure Appl. Chem., 71(6):1071-1074 (1999).
Joshi, R. A., et al., “A New and Improved Process for Celiprolol Hydrochloride,”Organic Process Research&Development, 5(2):176-178 (2001).
Gurjar, M. K., et al., “A novel and simple asymmetric synthesis of CMI-977 (LDP-977): a potent anti-asthmatic drug lead,”Tetrahedron: Asymmetry, 14:1363-1370 (2003).
Yasuhara, A., et al., “Deprotection ofN-Sulfonyl Nitrogen-Heteroaromatics With Tetrabutylammonium Fluoride,”Tetrahedron Letters, 39:595-596 (1998).
Maligres, P. E., et al., “Nosylaziridines: Activated Aziridine Electrophiles,”Tetrahedron Letters, 38(30):5253-5256 (1997).
Vedejs, E., et al., “Heteroarene-2-sulfonyl Chlorides (BtsCl; ThsCl): Reagents for Nitrogen Protection and >99% Racemization-Free Phenylglycine Activation with SOCl2,”J. Am. Chem. Soc., 118:9796-9797 (1996).
Corey, E. J., et al., “A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer Conditions,”J. Am. Chem. Soc., 119:12414-12415 (1997).
Bergeron, R., et al., “Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators,”J. Med. Chem., 42:95-108 (1999).
Bergeron, R. et al., “The Desferrithioc

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