Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2004-09-17
2009-12-01
Parsa, Jafar (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S561000, C560S115000
Reexamination Certificate
active
07626034
ABSTRACT:
The present invention relates to a process for producing amino acid derivatives such as optically active β-amino acid in short steps with good yield and high optical purity, which comprises reacting a keto acid of the formula (1):wherein R1is hydrogen, an optionally substituted hydrocarbon, etc.; R2is a spacer; and R3is an optionally substituted alkoxy, etc., or a salt thereof, with ammonia or an amine or a salt thereof in the presence of a chiral catalyst and in the presence or absence of an acid and/or a fluorine-containing alcohol, to give an amino acid derivative of the formula (2):wherein Q is a group formed by removing one hydrogen atom from ammonia or an amine; X′ is an acid and/or a fluorine-containing alcohol; and b is 0 or 1.
REFERENCES:
patent: 3644356 (1972-02-01), Chakrabarti et al.
patent: 4521624 (1985-06-01), Jackisch
patent: 4585887 (1986-04-01), Jolidon et al.
patent: 6646130 (2003-11-01), Rivera et al.
patent: 6884887 (2005-04-01), Riermeier et al.
patent: 6949677 (2005-09-01), Glufke et al.
patent: 7145030 (2006-12-01), Hamada et al.
patent: 7468459 (2008-12-01), Xiao et al.
patent: 2004/0147762 (2004-07-01), Zhang
Kadyrov et al., The First Highly Enantioselective Homogeneously Catalyzed Asymmetric Reductive Amination: Synthesis of -N-Benzylamino Acids, J. Org. Chem., 2003; 68(10); 4067-4070.
Tararov et al., On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes, Chem. Commun., 2000, 1867-1868.
Marigo et al., Direct catalytic asymmetric Mannich reactions of malonates and -keto esters, Chemistry—A European Journal (2003), 9(10), 2359-2367.
Marigo et al., Direct catalytic asymmetric Mannich reactions of malonates and □-keto esters, Chemistry—A European Journal (2003), 9(10), 2359-2367.
Zhou et al., Highly Effective Chiral Ortho-Substituted BINAPO Ligands (o-BINAPO): Applications in Ru-Catalyzed, Asymmetric Hydrogenations of b-Aryl-Substituted b-(Acylamino)acrylates and b-Keto Esters, Journal of the American Chemical Society (2002), 124(18), 4952-4953.
Mannich reaction, From Wikipedia, the free encyclopedia, page was last modified on Jun. 23, 2008.
Cohen et al., Stereoselective synthesis of .beta.-aryl-.beta.-amino esters, Tetrahedron Letters (2002), 43(11), 1977-1981.
R. Kadyrov et al., “The First Highly Enantioselective Homogeneously Catalyzed Asymmetric Reductive Amination: Synthesis of a-N-Benzylamino Acids”, Journal of Organic Chemistry, vol: 68, No. 10, pp. 4067-4070, 2003.
V. Tararov et al., “On the reductive amination of aldehydes and ketones catalyzed by homogeneous Rh(I) complexes”, Chemical Communications, pp. 1867-1868, 2000.
Gomez, S. et al., “The Reductive Amination of Aldehydes and Ketones and the Hydrogenation of Nitriles: Mechanistic Aspects and Selectivity Control,” Adv. Synth, Catal., 344:10, 2002, 1037-1057.
Tararov, V.I., et al., “A Scrutiny on the Reductive Amination of Carbonyl Compounds Catalyzed by Homogeneous Rh(I) Diphosphane Complexes,” Adv. Synth. Catal., 344:2, 2002, pp. 200-208.
Bunlaksananusorn, T. et al., “A Facile One-Pot Synthesis of Chiral beta-Amino Esters,” Synlett, No. 17, 2005, pp. 2682-2684.
Renat Kadyrov et al.; the First Highly Enantioselective Homogeneously Catalzyed Asymmetric Reductive Amination: Synthesis of a-N--Benzylamino Acids; J Org. Chemical 2003, 68, 4067-4070.
Vitali I. Tararov et al.; On the reducutive amination of adkehydes and ketones catalyzed by homogeneous Rh(I) complexes; Chemical Comun., 2000, 1867-1868.
Matsumura Kazuhiko
Saito Takao
Nwaonicha Chukwuma O
Parsa Jafar
Sughrue & Mion, PLLC
Takasago International Corporation
LandOfFree
Asymmetric reductive amination of keto acid derivatives for... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Asymmetric reductive amination of keto acid derivatives for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Asymmetric reductive amination of keto acid derivatives for... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4137734