Synthesis of substituted thiazoline carboxylic acids

Details Synthesis of substituted thiazoline carboxylic acids Synthesis of substituted thiazoline carboxylic acids

2007-10-23

2007-10-23

Saeed, Kamal A. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S201000

Reexamination Certificate

active

11242640

ABSTRACT:
A useful and efficient method of preparing an alkylated thiazoline carboxylic acid, or a derivative thereof, comprises coupling a substituted aryl nitrile such as, for example, 2,4-dimethoxybenzonitrile or 4-methoxybenzonitrile, with a cysteine ester to form a substituted thiazoline carboxylic acid ester; optionally hydrolyzing the substituted thiazoline carboxylic acid ester to form a substituted thiazoline carboxylic acid; optionally, protecting the carboxyl group; alkylating the thiazoline ring at the 4-carbon position, as indicated in Structural Formula (I), with a compound of the formula R1-L, wherein R1is as defined above and L is a leaving group, in the presence of a phase transfer catalyst; and, optionally, deprotecting the carboxyl group.In one embodiment of the present invention, a cinchona-alkaloid derived phase transfer catalyst is used to alkylate a protected substituted thiazoline carboxylic acid.

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: 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: 6982335 (2006-01-01), Chorghade et al.
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: 2004/0006224 (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
Ehrler, Juerg, and Farooq, Saleem, “Total Synthesis of Thiangazole,”Synlett,702-704 (1994).
Kishore, V., et al., “Synthesis of α-Poly-[NE-(2-aryl-Δ2-thiazoline-4-carbonyl)-L-lysines] With Antiviral Acitivity,”Indian Journal of Chemistry 15B:255-257 (1977).
Zamri, Adel, and Abdallah, Mohamed A., “An Improved Stereocontrolled Synthesis of Pyochelin, Siderophore ofPseudomonas aeruginosaandBurkholderia cepacia,” Tetrahedron56: 249-256 (2000).
Bergeron, R., et al., “Desazadesmethyldesferrithiocin Analogues as Orally Effective Iron Chelators,”J. Med. Chem.,42:95-108 (1999).
Bergeron, R. et al., “The Desferrithiocin Pharmacophore,”J. Med. Chem.,37:1411-1417 (1994).
Bergeron, R. et al., “Effects of C-4 Stereochemistry and C-4 Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues,”J. Med. Chem.,42:2432-2440 (1999).
Bergeron, R. et al., “Synthesis and Biological Evaluation of Naphthyldesferrithiocin Iron Chelators,”J. Med. Chem.,39:1575-1581 (1996).
Bergeron, R. et al., “Evaluation of Desferrithiocin and Its Synthetic Analogues as Orally Effective Iron Chelators,”J. Med. Chem.,34:2072-2078 (1991).
Bergeron, R. et al., “Evaluation of the Desferrithiocin Pharmacophore as a Vector for Hydroxamates,”J. Med. Chem.,42:2881-2886 (1999).
Bergeron, R. et al., “An Investigation of Desferrithiocin Metabolism,”J. Med. Chem.,37:2889-2895 (1994).
Bergeron, R. et al., “A Comparative Study of the Iron-Clearing Properties of Desferrithiocin Analogues with Desferrioxamine B in aCebusMonkey Model,”Blood,81(8):2166-2173 (1993).
Bergeron, R. et al., “Pharmacokinetics of Orally Administered Desferrithiocin Analogs inCebus ApellaPrimates,”Drug Metabolism and Disposition,27(12):1496-1498 (1999).
Corey, E. J., et al., “A Rational Approach to Catalytic Enantioselective Enaolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt Under Phase Transfer Conditions,”J. Am. Chem. Soc.,119:12414-12415 (1997).
Mulqueen, G. C., et al., “Synthesis of the Thiazoline-based Siderophore (S)-Desferrithiocin,”Tetrahedron,49(23):5359-5364 (1993).
O'Donnell, M. J., et al., “α-Methyl Amino Acids by Catalytic Phase-Transfer Aklylations,”Tetrahedron Letters,23(41):4259-4262 (1982).

Affiliated with

Also associated with

Rating

Synthesis of substituted thiazoline carboxylic acids does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of substituted thiazoline carboxylic acids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of substituted thiazoline carboxylic acids will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3888618