Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-04-17
1999-08-17
Kumar, Shailendra
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548215, 548225, 560 27, 560115, 560123, 560129, 564315, 564323, 564192, 564161, 564219, 564185, 564189, 564217, 564190, C07D26338, C07C21154, C07C23300, C07C 6720
Patent
active
059395540
ABSTRACT:
A method for preparing a diarylalanine compound is provided. The method includes reacting a diarylaminopropanediol with a reducing agent to form a diarylaminopropanol compound and/or contacting a serine ester derivative with an aryl metal reagent to form diarylaminopropanediol. A diarylmethyloxazolidinone compound is also provided.
REFERENCES:
patent: 4766109 (1988-08-01), Czarniecki et al.
patent: 5198548 (1993-03-01), Beylin et al.
patent: 5264577 (1993-11-01), Beylin et al.
Brunner et al, Journal of Organometallic Chemistry, 501, pp. 161-166, 1995.
Journal of Organic Chemistry, 1976,41(19)3219-20--Hansen,John F;Sep. 17, 1976.
Tetrahedron Letters, 1995,36(31)5619-5622--Koskinen,Ari M.P. et al, 1995.
Beaulieu, et al., "Enantiospecific Synthesis of D-.alpha., .omega.-Diaminoalkanoic Acids", Tetrahedron Letters, 29: 2019-2022 (1988).
Beaulieu, et al., "Synthesis of Chiral Vinylglycines", J. Org. Chem., 56: 4196-4204 (1991).
Bertozzi, et al., "Synthesis of Carbon-Linked Glycopeptides as Stable Glycopeptide Models", J. Org. Chem., 57: 6092-6094 (1992).
Beylin et al., "Cyclic Derivatives of 3,3-Diphenylalanine (DIP) (II), Novel .alpha.-Amino Acids for Peptides of Biological Interest", Tetrahedron Letters, 34: 953-956 (1993).
Burckhalter, et al., "Synthesis of Phenylalanine Analogs as Antimetabolites", J. Am. Chem. Soc., 73: 56-58 (1951).
Burgess, et al., "Asymmetric Syntheses of Optically Active .alpha.,.beta.-Disubstituted .beta.-Amino Acids", J. Org. Chem., 58: 4758-4763 (1993).
Chassaing, et al., "Synthesis of conformationally constrained phenylalanines and their incorporation into tachykinins", Peptides Chemistry, Structure and Biology, Proceedings of the Eleventh American Peptide Symposium, pp. 935-936 (1989).
Chen, et al., "Chiral Synthesis of D-and L-3,3-Diphenylalanine (DIP), Unusual .alpha.-Amino Acids for Peptides of Biological Interest", Tetrahedron Letters, 33: 3293-3296 (1992).
Evans, et al., "Asymmetric Alkylation Reactions of Chiral Imide Enolates. A Practical Approach to the Enantioselective Synthesis of .alpha.-Substituted Carboxylic Acid Derivatives", J. Am. Chem. Soc., 104: 1737-1739 (1982).
Evans, et al., "The Asymmetric Synthesis of .alpha.-Amino Acids. Electrophilic Azidation of Chiral Imide Enolates, a Practical Approach to the Synthesis of (R)- and (S)-.alpha.-Azido Carboxylic Acids", J. Am. Chem. Soc., 112: 4011-4030 (1990).
Filler, et al., "A New Synthesis of .beta.,.beta.-Diphenylalanine and Related Unnatural .alpha.-Amino Acids", J. Org. Chem., 26: 1685 (1961).
Filler, et al., "Synthetic Routes to .beta.,.beta.-Diaryl-.alpha.-Amino Acids via Nitrogen Hetercycles (l)", J. Het. Chem., 1: 153-157 (1964).
Gage, et al., "Diastereoselective Aldol Condensation Using a Chiral Oxazolidinone Auxiliary: (2S*, 3S*)-3-Hydroxy-3-Phenyl-2-Methylpropanoic Acid", Organic Synthesis, 68: 83-89 (1989).
Goodson, et al., "Potential Growth Antagonists. I. Hydantoins and Disubstituted Glycines", J. Org. Chem., 25: 1920-1924 (1960).
Hsieh, et al., "Topographic Probes of Angiotensin and Receptor: Potent Angiotensin II Agonist Containing Diphenylalanine and Long-Acting Antagonists Containing Biphenylalanine and 2-Indian Amino Acid in Position", J. Med. Chem., 32: 898-903 (1989).
Josien, et al., "Asymmetric Synthesis of L-Dihenylalanine and L-9-Fluorenylglycine via Room Temperature Alkylations of a Sultam-Derived Glycine Imine", Tetrahedron Lettersr, 32: 6547-6550 (1991).
Kanemasa, et al., "New Chiral Auxiliaries Based on Conformation Control, a C.sub.2 -Symmetric 2,2-Dimethylimidazolidine and 4-Chiral 2,2-Dialkyloxazolidines. Synthesis and Conformational Analysis of Acrylamide Derivatives", Tetrahedron, 48: 8631-8644 (1992).
Krysin, et al., "Electrochemical Synthesis of .alpha.-Amino Acids", Soviet Electrochemistry, 12: 1449-1451 (1976).
Luly, et al., "A Synthesis of Protected Aminoalkyl Expoxides from .alpha.-Amino Acids", J. Org. Chem., 52: 1487-1492 (1987).
Mustafa, et al., "Action of Grignard Reagents. XXII. Action of Organomagnesium Compounds on 2-Mercapto-4-arylidene-5-thiazolidones and on 4-Arylidene-2, 5-thiazolidinediones. Reaction of 2-Mercapto-4-benzylidene-5-thiazolidone with Diazomethane", J. Org. Chem., 26: 1782-1786 (1961).
O'Donnell, et al., "The Stereoselective Synthesis of .alpha.-Amino Acids by Phase-Transfer Catalysis", J. Am. Chem. Soc., 111: 2353-2355 (1989).
Sasaki, et al., "Stereoselective Synthesis of Optically Pure .beta.,.gamma.-Unsaturated .alpha.-Amino Acids in Both L and D Configurations", Tetrahedron Letters, 30: 1943-1946 (1989).
Shimamoto, et al., "A New Entry to the Synthesis of .beta.-Hydroxytyrosines Via A Novel Benzylic Hydroxylation", Tetrahedron Letters, 29: 5177-5180 (1988).
Sep. 17, 1976, Journal of Organic Chemistry, 1976, 41(19)3219-20--Hansen, John F.
Tetrahedron Letters, 1995, 36(31)5619-5622--Koskinen, Ari M.P. et al.
Despande Prasad K.
LaLoggia Anthony J.
Sibi Mukund P.
Kumar Shailendra
NDSU - Research Foundation
Padmanabhan Sreeni
LandOfFree
Diarylaminopropanediol and diarylmethyl-oxazolidinone compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Diarylaminopropanediol and diarylmethyl-oxazolidinone compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Diarylaminopropanediol and diarylmethyl-oxazolidinone compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-315930