Process for producing an optically active compound

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C548S469000

Reexamination Certificate

active

07816541

ABSTRACT:
The present invention provides a process for selectively producing an enantiomer at position 4 of an optically active compound in the cross aldol reaction of pyruvic acid and indole-3-pyruvic acid. The process comprises the step of reacting pyruvic acid with indole-3-pyruvic acid in the presence of an optically active α-amino acid containing a secondary amine and a metal ion.

REFERENCES:
patent: 5994559 (1999-11-01), Abushanab et al.
patent: 7064219 (2006-06-01), Kawahara et al.
patent: 7241599 (2007-07-01), Sugiyama et al.
patent: 7297800 (2007-11-01), Sugiyama et al.
patent: 7351569 (2008-04-01), Sugiyama et al.
patent: 7371549 (2008-05-01), Sugiyama et al.
patent: 7390909 (2008-06-01), Kawahara et al.
patent: 7396941 (2008-07-01), Mori et al.
patent: 7402412 (2008-07-01), Sugiyama et al.
patent: 7432100 (2008-10-01), Sugiyama et al.
patent: 7534590 (2009-05-01), Mori et al.
patent: 7534898 (2009-05-01), Amino et al.
patent: 7572607 (2009-08-01), Hicks et al.
patent: 7582455 (2009-09-01), Brazeau et al.
patent: 7612214 (2009-11-01), Amino et al.
patent: 2004/0063175 (2004-04-01), Abraham et al.
patent: 2005/0020508 (2005-01-01), Amino et al.
patent: 2005/0106305 (2005-05-01), Abraham et al.
patent: 2005/0112260 (2005-05-01), Abraham et al.
patent: 2005/0170041 (2005-08-01), Abraham et al.
patent: 2005/0221455 (2005-10-01), McFarlan et al.
patent: 2005/0244937 (2005-11-01), Abraham et al.
patent: 2005/0272939 (2005-12-01), Amino et al.
patent: 2005/0282260 (2005-12-01), Hicks et al.
patent: 2006/0003426 (2006-01-01), Sugiyama et al.
patent: 2006/0009394 (2006-01-01), Amino
patent: 2006/0074249 (2006-04-01), Kawahara et al.
patent: 2006/0252135 (2006-11-01), Brazeau et al.
patent: 2007/0072277 (2007-03-01), Sugiyama et al.
patent: 2007/0099277 (2007-05-01), Anderson et al.
patent: 2007/0105938 (2007-05-01), Anderson et al.
patent: 2008/0020434 (2008-01-01), Brazeau et al.
patent: 2008/0020435 (2008-01-01), Burke et al.
patent: 2008/0193975 (2008-08-01), Sugiyama et al.
patent: 2008/0193984 (2008-08-01), Sugiyama et al.
patent: 2008/0199921 (2008-08-01), Sugiyama et al.
patent: 2008/0274518 (2008-11-01), Hicks et al.
patent: 2008/0318290 (2008-12-01), Sugiyama et al.
patent: 2009/0117625 (2009-05-01), Abraham et al.
patent: 2009/0259052 (2009-10-01), Kawahara et al.
patent: 1749402 (2006-03-01), None
patent: 2002-60382 (2002-02-01), None
patent: 2004-331650 (2004-11-01), None
patent: WO 03/056026 (2003-07-01), None
patent: WO 03/059865 (2003-07-01), None
patent: WO 2004-067494 (2004-08-01), None
U.S. Appl. No. 12/613,713, filed Nov. 6, 2009, Kawahara, et al.
Kozo Nakamura, et al., “Total Synthesis of Monatin”, Organic Letters, vol. 2, No. 19, Aug. 25, 2000, pp. 2967-2970.
Cedric W. Holzapfel, et al. “A Simple Cycloaddition Approach to a Racemate of the Natural Sweetener Monatin”, Synthetic Communications, vol. 24, No. 22, 1994, pp. 3197-3211.
Cedric W. Holzapfel, et al. “The Synthesis of A γ-Keto-α-Amino Acid, A Key Intermediate in the Synthesis of Monatin, a New Natural Sweetener”, Synthetic Communications, vol. 23, No. 18, 1993, pp. 2511-2526.
Davi de Jesus Oliveira, et al., “Diastereoselective formation of a quaternary center in a pyroglutamate derivative. Formal synthesis of Monatin”, Tetrahedron Letters, vol. 42, 2001, pp. 6793-6796.
Nicholas Gathergood, et al., “Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism”, Org. Biomol. Chem., vol. 2, 2004, pp. 1077-1085.
Karsten Juhl, et al., “Catalytic asymmetric homo-aldol reaction of pyruvate—a chiral Lewis acid catalyst that mimics aldolase enzymes”, Chem. Commun., 2000, pp. 2211-2212.
Paolo Dambruoso, et al., “Efficiency in Isotetronic Acid Synthesis via a Diamine—Acid Couple Catalyzed Ethyl Pyruvate Homoaldol Reaction”, Organic Letters, vol. 7, No. 21, 2005, pp. 4657-4660.
U.S. Appl. No. 11/951,395, filed Dec. 6, 2007, Kawahara, et al.
U.S. Appl. No. 12/613,839, filed Nov. 6, 2009, Sugiyama, et al.
105,696, filed Jun. 25, 2009, Kawahara, et al.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for producing an optically active compound does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for producing an optically active compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing an optically active compound will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4207961

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.