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Ashton, W. T.; Cantone, C. L.; Tolman, R. L.; Greenlee, W. J.; Lynch, R. J.; Schorn, T. W.; Strouse, J. F.; Siegl, P. K. S. Inhibitors of Human Renin with C-Termini Derived from Amides and Esters of α-Mercaptoalkanoic Acids. J. Med. Chem. 1992, 35, 2772–2781.
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Doherty, A. M.; Sircar, I.; Kornberg, B. E.; Quin, J., III; Winters, R. T.; Raitenbronn, J. S.; Taylor, M. D.; Batley, B. L.; Rapundalo, S. R.; Ryan, M. J.; Painchaud, C. A. Design and Synthesis of Potent, Selective, and Orally Active Fluorine-Containing Renin Inhibitors. J. Med. Chem. 1992, 35, 2–14.
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Kleinert, H. D.; Rosenberg, S. H.; Baker, W. R.; Stein, H. H.; Klinghofer, V.; Barlow, J.; Spina, R.; Polakowski, J.; Kovar, P.; Cohen, J.; Dennisen, J. Discovery of a Peptide-Based Renin Inhibitor with Oral Bioavailability and Efficacy. Science 1992, 257, 1940–1943.
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Bolis, G.; Fung, A. R. L.; Greer, J.; Kleinert, H. D.; Marcotte, P. A.; Perun, T. J.; Plattner, J. J.; Stein, H. H. Renin Inhibitors. Dipeptide Analogues of Angiotensinogen Incorporating Transition-State, Nonpeptidic Replacements at the Scissile Bond. J. Med. Chem. 1987, 30, 1729–1737.
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Rempf, D. J.; Lara, E.; Stein, H. H.; Cohen, J.; Plattner, J. J. Renin Inhibitors Based on Novel Dipeptide Analogues. Incorporation of the Dehydrohydroxyethylene Isostere at the Scissile Bond. J. Med. Chem. 1987, 30, 1978–1983.
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Dellaria, J. F.; Maki, R. G.; Bopp, B. A.; Cohen, J.; Kleinert, H. D.; Luly, J. R.; Merits, L; Plattner, J. J.; Stein, H. H. Optimization and In Vivo Evaluations of a Series of Small, Potent, and Specific Renin Inhibitors Containing a Novel Leu-Val Replacement. J. Med. Chem. 1987, 30, 2137–2144.
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Boger, J.; Payne, L. S.; Perlow, D. S.; Lohr, N. S.; Poe, M.; Blaine, E. H.; Ulm, E. H.; Schorn, T. W.; Lamont, B.; Lin, T. Y.; Kawai, M.; Rich, D. H.; Veber, D. F. Renin Inhibitors. Syntheses of Subnanomolar, Competitive, Transition-State Analogue Inhibitors Containing a Novel Analogue of Statine. J. Med. Chem. 1985, 28, 1779–1790.
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An Efficient Synthesis of Optically Active-α-(t-Butoxycarbonylamino)-aldehydes from α-Amino Acids
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The Weinreb amide 1 is extremely stable and can be safely stored at room temperature. The procedure for preparing aldehyde 2 via the stable Weinreb amide was developed by Dr. Harold Weiler. For similar synthesis of various α-amino aldehydes, see
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The Weinreb amide 1 is extremely stable and can be safely stored at room temperature. The procedure for preparing aldehyde 2 via the stable Weinreb amide was developed by Dr. Harold Weiler. For similar synthesis of various α-amino aldehydes, see: (a)Fehrentz, J.-A.; Castro, B. An Efficient Synthesis of Optically Active-α-(t-Butoxycarbonylamino)-aldehydes from α-Amino Acids. Synthesis 1983, 676–678
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Tetrapeptides with Enhanced Aqueous Solubility and Nanomolar Potency
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For alternate preparations of α-amino aldehyde 2, see ref 9 and the following
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For alternate preparations of α-amino aldehyde 2, see ref 9 and the following: (a)Bock, M. G.; Dipardo, R. M.; Evans, B. E.; Freidinger, R. M.; Rittle, K. E.; Payne, L. S.; Boger, J.; Whitter, W. L.; LaMont, B. I.; Ulm, E. H.; Blaine, E. H.; Schorn, T. W.; Veber, D. F. Renin Inhibitors Containing Hydrophilic Groups. Tetrapeptides with Enhanced Aqueous Solubility and Nanomolar Potency. J. Med. Chem. 1988, 31, 1918–1923.
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0001582498
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Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. A Synthesis of Protected Aminoalkyl Epoxides from α-Amino Acids. J. Org. Chem. 1987, 52, 1487–1492.
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For preparation of configurationaly stable N-protected α-amino aldehydes
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For preparation of configurationaly stable N-protected α-amino aldehydes, see:Lubell, W. D.; Rapoport, H. Configurational Stability of N-Protected α-Amino Aldehydes. J. Am. Chem. Soc. 1987, 109, 236–239.
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For a preliminary communication on the preparation of fluoro ketone 11, see
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For a preliminary communication on the preparation of fluoro ketone 11, see:Patel, D. V.; Rielly-Gauvin, K.; Ryono, Denis, E. Peptidic Trifluoromethyl Alcohols and Ketones. A General Synthesis and Application as Renin Inhibitors. Tetrahedron Lett. 1988, 29, 4665–4668.
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Bergeson, S. H.; Edwards, P. D.; Krell, R. D.; Shaw, A.; Stein, R. L.; Stein, M. M.; Strimpler, A. M.; Trainor, D. A.; Wildonger, R. A.; Wolanin, D. J. Inhibition of Human Leukocyte Elastase by Peptide Trifluoromethyl Ketones. In Abstracts of Papers; 193rd National Meeting of the American Chemical Society, Denver, Colorado, April 5–10, 1987; American Chemical Society: Washington DC, 1987; MEDI 0001.
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Shioiri, T.; Ninomiya, K.; Yamada, S-I. Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis. J. Am. Chem. Soc. 1972, 94, 6203–6205.
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1 Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones. J. Org. Chem. 1983, 48, 4155–4156.
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Dess-Martin oxidation is one of the best methods available for oxidation of alcohols bearing electron-deficient groups to the corresponding activated ketones. For the first application of this reagent toward the preparation of trifluoromethyl ketones, see, For a detailed account, see
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Dess-Martin oxidation is one of the best methods available for oxidation of alcohols bearing electron-deficient groups to the corresponding activated ketones. For the first application of this reagent toward the preparation of trifluoromethyl ketones, see: (a)Linderman, R. J.; Graves, D. M. An Efficient Procedure for the Oxidation of Fluorinated Carbinols. Tetrahedron Lett. 1987, 28, 4259–4262. For a detailed account, see
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Application of the Dakin-West Reaction to the Synthesis of Imidazo-[5,1-f]-1,2,4-[triazin-4(3H)-ones
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Charles, I.; Latham, D. W. S.; Hartley, D.; Oxford, A. W.; Scopes, D. I. C. Bicyclic Heterocycles with Nitrogen at the Ring Junction. Part 2. Application of the Dakin-West Reaction to the Synthesis of Imidazo-[5,1-f]-1,2,4-[triazin-4(3H)-ones. J. Chem. Soc., Perkin Trans. 1, 1980, 1139–1146
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Application of α-hydroxy ester based peptides as renin inhibitors was reported right after our own work was completed. See
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Application of α-hydroxy ester based peptides as renin inhibitors was reported right after our own work was completed. See: (a)Iizuka, K.; Kamijo, T.; Kubota, T.; Akahane, K.; Umeyama, H.; Kiso, Y. New Human Renin Inhibitors Containing an Unnatural Amino Acid, Norstatine. J. Med. Chem. 1988, 31, 701–704.
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Hengeveld, J. E.; Grief, V.; Tadanier, J.; Lee, C.-M.; Riley, D.; Lartey, P. A. A General Synthesis of Methyl Aldulosonates Using Tris-(Methylthio) Methyl Lithium as the Ester Anion Equivalent. Tetrahedron Lett. 1984, 25, 4075–4078.
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85022273700
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For preparation of 29, see:Weller, H. N. III; Ryono, D. E. US Patent 5,055,466.
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