Process for the preparation of dihydroxy esters and...

Chemistry: molecular biology and microbiology – Micro-organism – tissue cell culture or enzyme using process... – Preparing oxygen-containing organic compound

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C435S195000, C514S547000, C560S186000

Reexamination Certificate

active

07732171

ABSTRACT:
A process is provided for the preparation of a compound of formula (1)wherein R and R′ represent optionally substituted hydrocarbyl groups and X represents a hydrocarbyl linking group. The process comprises either the stereoselective reduction of the keto group in a dihydroxy keto precursor followed by selective esterification of a primary hydroxy, or selective esterification of a primary hydroxy of a dihydroxy keto precursor followed by stereoselective reduction of the keto group.

REFERENCES:
patent: 3325466 (1967-06-01), Anderson et al.
patent: 3992432 (1976-11-01), Napier et al.
patent: 4248889 (1981-02-01), Oka et al.
patent: 5278313 (1994-01-01), Thottathil et al.
patent: 5457227 (1995-10-01), Thottathil et al.
patent: 5559030 (1996-09-01), Matsuyama et al.
patent: 5594153 (1997-01-01), Thottathil et al.
patent: 5700670 (1997-12-01), Yamagishi et al.
patent: 6001618 (1999-12-01), Kimoto et al.
patent: 6225099 (2001-05-01), Hummel 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: 6472544 (2002-10-01), Kizaki 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: 6903225 (2005-06-01), Kizaki et al.
patent: 7094594 (2006-08-01), Nishiyama et al.
patent: 7157255 (2007-01-01), Blacker et al.
patent: 7416865 (2008-08-01), Blacker et al.
patent: 2006/0004200 (2006-01-01), Gudipati et al.
patent: 2006/0040898 (2006-02-01), Puthiaparampil et al.
patent: 0 569 998 (1993-11-01), None
patent: 0 579 370 (1994-01-01), None
patent: 0 606 899 (1994-07-01), None
patent: 0 737 751 (1996-10-01), None
patent: 0 796 914 (1997-09-01), None
patent: 0 862 646 (1998-09-01), None
patent: 1 024 139 (2000-08-01), 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 97/00968 (1997-01-01), 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 00/36134 (2000-06-01), None
patent: WO 00/49014 (2000-08-01), None
patent: WO 00/68221 (2000-11-01), None
patent: WO 01/04336 (2001-01-01), 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 2004/108691 (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 2006/067456 (2006-06-01), None
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).
Patel et al. “Enantioselective microbial reduction of 3,5-dioxo-6-(benzyloxy) hexanoic acid, ethyl ester” Enzyme Microb. Technol. 15: 1014-1021 (1993).
Peters et al. “Studies on the distribution and regulation of microbial keto ester reductases” Applied Microbiolgy Biotechnology 38: 334-340 (1992).
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.
Shao et al. “Asymmetric hydrogenation of 3,5-Dioxoesters catalyzed by Ru-binap complex: A short step asymmetric synthesis of 6-substituted 5,6-dihydro-2-pyrones” Tetrahedron 49(10):1997-2010 (1993).
Barry et al. (1982) Easy and Efficient Anion Alkylations in Solid-Liquid PTC Conditions, Tetrahedron Lett. 23(51):5407-5408.
Barry et al. (1983) Alkylations En Absence De Solvant Orgamque. Effets D'Addition D'Oxydes Mineraux Et De Sels D'Ammonium-II, Tetradron 39(16):2673-2677.
Bennett et al. (1991) Methyl (3R)-3-Hydroxyhex-5-Enoate As A Precursor To Chiral Mevinic Acid Analogues, J. Chem. Soc. 1:133-140.
Bram et al. (1985) Anionic Activation By Solid-Liquid Phase Transfer Catalysis Without Solvent: An Improvement In Organic Synthesis, Israel J. Chem. 26:291-298.
Chevallett et al. (1993) Facile Synthesis Of Tert-Butyl Ester of N-Protected Amino Acids With Ter-Butyl Bromide, Tetrahedron Lett. 34(46):7409-7412.
Chikara et al. (1993) Preparation Of Optically Active 5,6-Epoxyhexanoic Acid Esters As Materials For Physiologically Active Substances, 6001 Chemical Abstracts, 118(11):101787x.
Crowther et al. (1971) Esterification of Hindered Alcohols:tert-Butylp-Toluate, Organ. Synth. 51, 96, pp. 259-262.
Halpern (1997) Choosing a Phase-Transfer Catalyst, Phase-Transfer Communications, 3(1):1-16.
Inanaga et al. (1979) A Rapid Esterification By Means Of Mixed Anhydride And Its Application To Large-Ring Lactonization, Bull. Chem. Soc. Jpn., 52(7):1989-1993.
March (1992) Advanced Organic Chemistry; Reactions, Mechanisms and Structure, p. 392.
Murakami et al. (1990) 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.
Murphy et al. (1970) Chemistry of Cephalosporin Antibiotics. XVIII. Synthesis of 7-Acyl-3-Methyl-2-Cephem-4-Carboxylic Acid Esters, J. Org. Chem. 35(7):2429-2430.
Rayle et al. (1999) Development Of A Process For Triazine-Promoted Amidation of Carboxylic Acids, Org. Proc. Res. & Dev. 3:172-176.
Sakaki et al. (1991) Lipase-Catalyzed Asymmetric Synthesis of 6-(3-Chloro-2-Hydroxypropyl)-1,3-Dioxin-4-Ones And Their Conversion to Chiral 5,6-Epoxyhexanoates, Tetrahedron Asymmetry 2(5):343-346.
Takeda et al. (Oct. 1994) Dicarbonates: Convenient 4-Dimethylaminopyridine Catalyzed Esterification Reagents, Synthesis, pp. 1063-1066.
Thierry et al. (1998) 2-Phenyl Isopropyl and t-Butyl Trichloroacetimidates: Useful Reagents For Ester Preparation of N-Protected Amino Acids Under Neutral Conditions, Tetrahedron Lett. 39:1557-1560.
Watanabe et al. (1997) Synthesis and Biological Activity of Methanesulfonamide Pyrimidine-AndN-Methanesulfonyl Pyrrole-Substituted 3,5-Dihydroxy-6-Heptenoates, A Novel Series of HMG-CoA Reductase Inhibitors, Bioorg. Med. Chem. 5(2):437-444.
Watanabe et al. (1999) ZD-4522 Hypolipidemic HMG-CoA Reductase Inhibitor, Drugs of the Future, 24(5):511-513.
Wessenfels et al. (1972) Substituierte 2-Formylmethylen-2H-1-Benzopyrane Aus β-Chlorvinylaldehyden, Z Chem. 12(7):263-265.
Ziegler et al. (1979) A Mild Method for the Esterification of Fatty Acids, Synth. Comm. 9(6):539-543.
Phase Transfer Catalysis, Principles , And Techniques (C.M. Starks; Academic Press, 1978), pp. 140-147.

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process for the preparation of dihydroxy esters and... 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 dihydroxy esters and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of dihydroxy esters and... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4245196

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.