Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2011-08-02
2011-08-02
Oh, Victor (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
07989643
ABSTRACT:
The invention relates to the preparation of 2-(6-substituted-1,3-dioxane-4-yl)acetic acid derivatives of formula 1, where X stands for a leaving group, and R1, R2, and R3each independently stand for an alkyl group with 1-3 carbon atoms from 4-hydroxy-6-X-substituted-methyl-tetrahydropyran-2-one compounds, where X is as defined above, with the aid of an acetalization agent, in the presence of an acid catalyst.The invention also relates to the novel compounds of formula 1 as well as salts and acids to be prepared from these, with the OR3group in formula 1 being replaced by an OY group, where X, R1and R2have the meanings defined above and where Y stands for an alkaline (earth) metal or a substituted or unsubstituted ammonium group or stands for hydrogen, and to the novel compounds of formula 2.The products concerned are, after conversion into the t-butyl ester of 2-(6-hydroxymethyl-1,3-dioxane-4-yl)acetic acid, important as intermediary products in the preparation of statins.
REFERENCES:
patent: 3325466 (1967-06-01), Anderson et al.
patent: 3992432 (1976-11-01), Napier et al.
patent: 5278313 (1994-01-01), Thottathil et al.
patent: 5292891 (1994-03-01), Kaneko et al.
patent: 5294724 (1994-03-01), Jendralla et al.
patent: 5443970 (1995-08-01), Blacker et al.
patent: 5449793 (1995-09-01), Miyazawa et al.
patent: 5457227 (1995-10-01), Thottathil et al.
patent: 5594153 (1997-01-01), Thottathil et al.
patent: 6278001 (2001-08-01), Solladie et al.
patent: 6331641 (2001-12-01), Taoka et al.
patent: 6340767 (2002-01-01), Nishiyama et al.
patent: 6344569 (2002-02-01), Mitsuda et al.
patent: 6784171 (2004-08-01), Taylor et al.
patent: 6844437 (2005-01-01), Taylor et al.
patent: 6870059 (2005-03-01), Kooistra et al.
patent: 7157255 (2007-01-01), Blacker et al.
patent: 7304156 (2007-12-01), Matsushita et al.
patent: 7416865 (2008-08-01), Blacker et al.
patent: 7442811 (2008-10-01), Bakel Van et al.
patent: 7511140 (2009-03-01), Horbury et al.
patent: 7524955 (2009-04-01), Newton et al.
patent: 7642363 (2010-01-01), Kooistra et al.
patent: 7718812 (2010-05-01), Hof et al.
patent: 7732171 (2010-06-01), Blacker et al.
patent: 7816528 (2010-10-01), Matshshita et al.
patent: 2006/0004200 (2006-01-01), Gudipati et al.
patent: 2006/0040898 (2006-02-01), Puthiaparampil et al.
patent: 2006/0293355 (2006-12-01), Booth et al.
patent: 2007/0105882 (2007-05-01), Black et al.
patent: 2007/0255060 (2007-11-01), Okada et al.
patent: 2008/0188657 (2008-08-01), Lenger et al.
patent: 2008/0207903 (2008-08-01), Butters et al.
patent: 2008/0221323 (2008-09-01), Crabb et al.
patent: 2009/0264654 (2009-10-01), Newton et al.
patent: 2009/0286819 (2009-11-01), Horbury et al.
patent: 2010/0209984 (2010-08-01), Blacker et al.
patent: 2010/0222373 (2010-09-01), Booth et al.
patent: 2010/0228028 (2010-09-01), Butters et al.
patent: 1024139 (2000-08-01), None
patent: 0862646 (2002-04-01), None
patent: 885516 (1961-12-01), None
patent: 4-266879 (1992-09-01), None
patent: WO 91/13876 (1991-09-01), None
patent: WO 93/06235 (1993-04-01), None
patent: WO 93/08823 (1993-05-01), None
patent: WO 96/31615 (1996-10-01), None
patent: WO 97/19185 (1997-05-01), None
patent: WO 97/19917 (1997-06-01), None
patent: WO 99/57109 (1999-11-01), None
patent: WO 00/08011 (2000-02-01), None
patent: WO 00/34264 (2000-06-01), None
patent: WO 00/49014 (2000-08-01), None
patent: WO 00/68221 (2000-11-01), None
patent: WO 01/72706 (2001-10-01), None
patent: WO 01/85975 (2001-11-01), None
patent: WO 02/06266 (2002-01-01), None
patent: WO 03/006439 (2003-01-01), None
patent: WO 03/059901 (2003-07-01), None
patent: WO 03/087112 (2003-10-01), None
patent: WO 03/106447 (2003-12-01), None
patent: WO 2004/014872 (2004-02-01), None
patent: WO 2004/054986 (2004-07-01), None
patent: WO 2004/103977 (2004-12-01), None
patent: WO 2004/108691 (2004-12-01), None
patent: WO 2004/113314 (2004-12-01), None
patent: WO 2005/023779 (2005-03-01), None
patent: WO 2005/028450 (2005-03-01), None
patent: WO 2005/042522 (2005-05-01), None
patent: WO 2005/063728 (2005-07-01), None
patent: WO 2006/067456 (2006-06-01), None
patent: WO 2007/007119 (2007-01-01), None
Bennett et al , Methyl(3R)-3-hydroxyhex-5-enoate as a Precursor to Chiral Mevinic Acid Analogues, 1991, J Chem Soc Perkin Transaction I, p. 133-140.
Barry et al. “Alkylations En Absence De Solvant Organique. Effets D'Addition D'Oxydes Mineraux Et De Sels D'Ammonium-II” Tetradron 39(16):2673-2677 (1983).
Barry et al. “Easy and efficient anion alkylations in solid-liquid PTC conditions” Tetrahedron Letters 23(51):5407-5408 (1982).
Bennett et al. “Methyl (3R)-3-hydroxyhex-5-enoate as a precursor to chiral mevinic acid analogues” J. Chem. Soc. 1:133-140 (1991).
Bram et al. “Anionic activation by solid-liquid phase transfer catalysis without solvent: an improvement in organic synthesis” Israel J. Chem. 26:291-298 (1985).
Chevallett et al. “Facile synthesis of tert-butyl ester of n-protected amino acids with tert-butyl bromide” Tetrahedron Letters 34(46):7409-7412 (1993).
Chikara et al. “Preparation of optically active 5,6-epoxyhexanoic acid esters as materials for physiologically active substances, Chemical Abstracts + Indexes” American Chemical Society, vol. 118, No. 11, p. 832, XP002178273 (1993).
Crowther et al. “Esterification of hindered alcohols: tert-butyl p-toluate” Organ. Synth. 51, 96, pp. 259-262 (1971).
Gijsen et al. “Recent advances in the chemoenzymatic synthesis of carbohydrates and carbohydrate mimetics” Chem. Rev. 96(1):443-473 (1996).
Greenberg et al. “Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates” PNAS 101(16):5788-5793 (2004).
Halpern, Choosing a phase-transfer catalyst, phase-transfer communications, 3(1):1-16 (1997).
Harris et al. “Acyl-CoA:Cholesterol O-Acyltransferase (ACAT) Inhibitors” J. Med. Chem. 35:4384-4392 (1992).
Inanaga et al. “A rapid esterification by means of mixed anhydride and its application to large-ring lactonization” Bull. Chem. Soc. Japan, 52(7):1989-1993 (1979).
International Search Report mailed on Oct. 9, 2001, for PCT patent application No. PCT/NL01/00535, filed on Jul. 12, 2001, 4 pages.
Kaneko et al. “Preparation of optically active 5,6-epoxyhexanoic acid esters as materials for physiologically active substances” Chemical Abstracts + Indexes, American Chemical Society, Columbus, US 118(11):832 (1993).
March, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed., John Wiley & Sons, Inc, p. 392 (1992).
March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed., John Wiley & Sons, Inc, p. 378 (1992).
Menges et al. “Oxidative degradation of γ-butyrolactons into 1,3-diols via a criegee rearrangement of peroxosulfonates. an enantioselective synthesis of compactin lactone and its diastereomer” Synlett 12:901-905 (1993).
Morrison and Boyd “Alkaline hydrolysis of esters” Lehrbuch der Organischen Chemie, 2nd ed., Verlag Chemie, p. 739 (1978) (Translation enclosed).
Murakami et al. “2,4,6-Tripyridinio-1,3,5-triazine trichloride, a new and mild esterification agent for preparation of penicillin esters” Heterocycles, 31(11):2055-2064 (1990).
Murphy et al. “Chemistry of cephalosporin antibiotics. XVIII. Synthesis of 7-acy1-3-methy1-2-cephem-4-carboxylic acid esters” J. Org. Chem 35(7):2429-2430 (1970).
Nebergall et al., College Chemistry with qualitative analysis, p. 89, 1980.
Phase Transfer Catalysis, Principles , and Techniques (C.M. Starks; Academic Press), pp. 140-147 (1978).
Presentation given at the 20th International Congress of Heterocyclic Chemistry in Palermo, Aug. 1-5, 2005.
Presentation given at the Gordon Conference on Heterocyclic Compounds, Salve Regina University, Newport, Rhode Island, Jul. 4-9, 2004.
Rayle et al. “Development of a process for triazine-promoted amidation of carboxylic acids” Org. Proc. Res. &
Kooistra Jacob Hermanus Mattheus Hero
Mink Daniel
Mulders Joannes Maria Cornelis Antonius
Zeegers Hubertus Josephus Marie
AstraZeneca UK Ltd.
Morgan & Lewis & Bockius, LLP
Oh Victor
LandOfFree
Process for the preparation of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2700136