Process for preparing the antiviral agent [1S-(1alpha, 3alpha, 4beta)]-2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)-3-methylenecyclopentyl]-6H-purin-6-one
Processes are disclosed for preparing the antiviral agent entecavir. A resin adsorption process for the isolation and purification of entecavir is also disclosed. Various intermediates useful in the preparation of entecavir are also disclosed.
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Format | Patent |
Language | English |
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02.06.2009
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Abstract | Processes are disclosed for preparing the antiviral agent entecavir. A resin adsorption process for the isolation and purification of entecavir is also disclosed. Various intermediates useful in the preparation of entecavir are also disclosed. |
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AbstractList | Processes are disclosed for preparing the antiviral agent entecavir. A resin adsorption process for the isolation and purification of entecavir is also disclosed. Various intermediates useful in the preparation of entecavir are also disclosed. |
Author | Rijhwani, Sushil K Chan, Yeung Yu |
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References | Griffith, D.A. et al., "The Total Synthesis of Allosamidin. Expansions of the Methodology of Azaglycosylation Pursuant to the Total Synthesis of Allosamidin. A Surprising Enantiotopic Sense for a Lipase-Induced Deacetylation", J. Am. Chem. Soc., vol. 118, No. 40, pp. 9526-9538 (1996). Bisacchi, G.S. et al., "BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro," Bioorganic & Medicinal Chemistry Letters, vol. 7, Issue 2, 21 1997, pp. 127-132. Hanson et al. (4900847) 19900200 Ziegler, F.E., et al., "Radical cyclization studies directed toward the synthesis of BMS-200475 'entecavir': the carbocyclic core," Tetrahedron, vol. 59, Issue 45, Nov. 3, 2003, pp. 9013-9018. Fleming, I., "Silyl-to-Hydroxy Conversion in Organic Synthesis", Chemtracts-Organic Chemistry, vol. 9, pp. 1-64 (1996). Jones, G.R. et al., "The Oxidation of the Carbon-Silicon Bond", Tetrahedron, vol. 52, No. 22, pp. 7599-7662 (1996). Khanapure, S.P. et al., "An Efficient Synthesis of 4(S)-Hydroxycyclopent-2-enone", J. Org. Chem., vol. 60, No. 23, pp. 7548-7551 (1995). Zahler et al. (5206244) 19930400 DiMarco et al. (2007/0060599) 20070300 Pendri et al. (2006/0106216) 20060500 Danishefsky, S.J. et al., "Novel Stereospecific Silyl Group Transfer Reactions: Practical Routes to the Prostaglandins", J. Am. Chem. Soc., vol. 111, pp. 3456-3457 (1989). Li, G. et al., "N-Halocarbamate Salts Lead to More Efficient Catalytic Asymmetric Aminohydroxylation", Angew. Chem. Int. Ed. Engl., vol. 35, No. 23/24, pp. 2813-2817 (1996). Katsuki et al. (4471130) 19840900 Zhou et al. (2005/0272932) 20051200 Humiliere, D. et al., "A New Enantioselective Synthesis of Highly Functionalized Cyclopentanols," Synlett 1998, pp. 1255-1257. Bonini, C. et al., "A critical outlook and comparison of enantioselective oxidation methodologies of olefins", Tetrahedron, vol. 58, pp. 4981-5021 (2002). (WO 01/64221) 20010900 Pearson, A.J. et al., "Conjugate Additions of Carbon Nucleophiles to Cyclopentadienones," Organic Letters, vol. 5, No. 14, 2003, pp. 2547-2459. (WO 98/09964) 19980300 Greene, T.W. et al., Protective Groups in Organic Synthesis, Second Edition, John Wiley & Sons, Inc., publ., pp. 198-201 (1991). Miyaji, K. et al., "Synthesis of Corey Lactone Via Highly Stereoselective Asymmetric Diels-Alder Reaction", Tetrahedron Letters, vol. 32, No. 35, pp. 4557-4560, 1991. Katsuki et al. (4594439) 19860600 Carceller et al., "Synthesis of cis-bicyco [13.3.0]oct-3-ene-2, 7-dione, a highly functionalized cyclopentanoid intermediate," Tetrahedron Letters, vol. 25, Issue 19, 1984, pp. 2031-2034. |
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Snippet | Processes are disclosed for preparing the antiviral agent entecavir. A resin adsorption process for the isolation and purification of entecavir is also... |
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Title | Process for preparing the antiviral agent [1S-(1alpha, 3alpha, 4beta)]-2-amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)-3-methylenecyclopentyl]-6H-purin-6-one |
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