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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Main Authors Chan, Yeung Yu, Rijhwani, Sushil K
Format Patent
LanguageEnglish
Published 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.
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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