Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
2006-03-21
2006-03-21
Wilson, James O. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
C544S008000, C548S127000
Reexamination Certificate
active
07015321
ABSTRACT:
A practical and high-yielding method for the efficient, one-step synthesis of diverse classes of N,N′-differentiated sulfamides employs a wide range of amino alcohols and simple amines using Burgess-type reagents. This methodology extends the application and availability of sulfamides within the fields of chemical biology, medicinal chemistry, asymmetric synthesis, and supramolecular chemistry.
REFERENCES:
Lamberth, C. “Burgess Reagent ([Methoxycarbonylsulfamoyl]triethylammonium Hydroxide Inner Salt): Dehydrations and More” Journal für Praktische Chemie, vol. 342(5), pp. 518-522 (2000).
Winum et al, “N-(tert-Butoxycarbonyl)-N-[4-(dimethylazaniumlidene-1,4-dihydropyridin-1-ylsulfonyl]azanide: A New Sulfamoylating Agent. Structure and Reactivity toward Amines” Organic Letters, vol. 3(14), pp. 2241-2243 (2001).
Khapli et al, “Burgess Reagent in Organic Synthesis” Journal of the Indian Institute of Science, vol. 81(4), pp. 461-476 (Jul.-Aug. 2001).
Atkins, Jr.; et al., “The Reactions of an N-Sulfonylamine Inner Salt”,J. Am. Chem. Soc. 90: 4744-4745 (1968).
Burgess et al., “Synthetic Applications of N-Carboalkoxysulfamate Esters”,J. Am. Chem. Soc. 92: 5224-5226 (1970).
Atkins, Jr.; et al., “Synthesis and Reactions of N-Sulfonylamines”,J. Am. Chem. Soc. 94: 6135-6141 (1972).
Burgess, et al., “Thermal Reactions of Alkyl-N-Carbomethoxysulfamate Esters”,J. Org. Chem. 38: 26-31 (1973).
Davis, et al., “A new Synthesis of Primary Amines from Diarylidenesulfamides”,Tetrahedron Lett. 27: 3957-3960 (1986).
Rosenberg, et al., “Potent, Low Molecular Weight Renin Inhibitors Containing a C-Terminal Heterocycle: Hydrogen Bonding at the Active Site”,J. Med. Chem. 33: 1582-1590 (1990).
Oppolzer, et al., “Enantiomerically Pure, Crystalline ‘Anti’-Aldols from N-Acylbornanesultam: Aldolization and Structure of Intermediate t-butyldimethylsilyl-N,O-Ketene Acetal”,Tetrahedron Lett. 32: 61-64 (1991).
Oppolzer, et al., “Enantiomerically Pure Isoxazolines via Addition of Nitrile Oxides to Chiral N-Acryloyl Toluene-2,α-Sultams”,Tetrahedron Lett. 32: 4893-4896 (1991).
Sartor, et al., “Enantioselective Diels-Alder Reaction of Enals: Fighting Species Multiplicity of the Catalyst with Donor Solvents”,Tetrahedron Asymmetry 2: 639-642 (1991).
Ahn, et al., “Asymmetric Aldol Reactions Employing a Cyclic Sulfamide Chiral Auxiliary”,Tetrahedron Lett. 33: 6661-6664 (1992).
Castro, et al., “Synthesis and Biological Activity of 3-[2-(Dimethylamino)cthyl]-5-[(1, 1-dioxo-5-methyl-1,2,5-thiadiazolidin-2-yl)methyl]-H-indole and Analogues: Agonists for the 5-HTIDReceptor”,J. Med. Chem. 37: 3023-3032 (1994).
Taibe, P,; Mobashery, S. “(Methoxycarbonylsulfamoyl)triethylammonium hydroxide”, in Encyclopedia of Reagents for Organic Synthesis, vol. 5 (Ed. L. A. Paquette), John Wiley & Sons: Chichester, 1995, pp. 3345-3347.
Dewynter, et al., “Sulfonyl Bis-N-Oxazolidinone (SBO): A New Versatile Dielectrophile with Sequential Reactivity”,Tetrahedron Lett. 38: 8691-8694 (1997).
Pansare, et al., “Stereoselective Synthesis of 3,4-Disubstituted 1,2,5-Thiadiazolidine 1,1-Dioxides and Their conversion to Unsymmetrical Vicinal Diamincs”,Synlett: 623-624 (1998).
Tozer, et al., “4-Chlorobenzyl Sulfonamide and Sulfamide Derivatives of Histamine Homologues: The Design of Potent Histamine H3Receptor Antagonists”,Bioorg. Med. Chem. Lett. 9: 3103-3108 (1999).
Gong et al., “Polar Assembly of N,N'-Bis(4-substituted benzyl)sulfamides”,J. Am. Chem. Soc.121: 9766-9767 (1999).
Burckhardt, S., “Methyl N-(tricthylammonium-sulfonyl)carbamate: “Burgess Reagent””,Synlett: 559 (2000).
Kuang, et al., “Utilization of the 1,2,5-Thiadiazolidin-3-one 1,1-Dioxide Scaffold in the Design of Potent Inhibitors of Serine Proteases: SAR Studies Using Carboxylates”,Bioorg. Med. Chem. 8: 1005-1016 (2000).
Pete, et al., “Synthesis of 5-Substituted Indole Derviatives, Part II. Synthesis of Sumatriptan through the Japp-Klingermann Reaction”,Heterocycles 53: 665-673 (2000).
Dougherty, et al., “Ring-Closing Metathesis Strategies to Cyclic Sulfamide Peptidomimetics”,Tetrahedron 56: 9781-9790 (2000).
Hof, et al., “Emergent Conformational Preferences of a Self-Assembling Small Molecule: Structure and Dynamics in a Tetrameric Capsule”,J. Am. Chem. Soc. 122: 10991-10996 (2000).
Schaal, et al., “Synthesis and Comparative Molecular Field Analysis (CoMFA) of Symmetric and Nonsymmetric Cyclic Sulfamide HIV-1 Protease Inhibitors”,J. Med. Chem. 44: 155-169 (2001).
Hof, et al., “Highly slective Synthesis of Heterosubstituted Aromatic Sulfamides”,Organic Letters 3: 4247-4249 (2001).
Wood, et al., “A novel, one-step method for the conversion of primary alcohols into carbamate-protected amines”,Tetrahedron Lett. 43: 3887-3890 (2002).
Nicolaou, et al., “A Novel Regio- and Steroselective Synthesis of Sulfamidates from 1,2-Diols Using Burgess and Related Reagents: A Facile Entry into β-Amino Alcohols”,Angew. Chem. Int. Ed. Engl. 41: 834-838 (2002).
Huang Xianhai
Longbottom Deborah
Nicolaou Kyriacos C.
Snyder Scott A.
Lewis Donald G.
The Scripps Research Institute
Tucker Zachary C.
Wilson James O.
LandOfFree
Synthesis of non-symmetrical sulfamides using burgess-type... 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 non-symmetrical sulfamides using burgess-type..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of non-symmetrical sulfamides using burgess-type... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3609578