- Development of a biocatalytic process as an alternative to the (-)-DIP-Cl-mediated asymmetric reduction of a key intermediate of montelukast
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A KetoREDuctase (KRED) engineered via directed evolution technologies catalyzed the asymmetric reduction of (F)-methyl 2-(3- (3-(2-(7-chloroquinolin- 2-yl)vinyl)phenyl)-3-oxopropyl)benzoate to the corresponding (S)-alcohol, a key intermediate in the synth
- Liang, Jack,Lalonde, James,Borup, Birthe,Mitchell, Vesna,Mundorff, Emily,Trinh, Na,Kochrekar,Cherat, Ramachandran Nair,Ganesh Pai
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Read Online
- A graphene palladium-copper catalytic synthesis meng the Ruse special sodium chiral is mellow intermediates (by machine translation)
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The invention discloses a novel graphene palladium-copper with chiral diphosphine ligand composite catalytic synthesis intermediate meng the Ruse special sodium chiral is mellow [S - (E)] - 2 - [3 - [3 - [2 - (7 - chloro - 2 - quinolyl) vinyl] phenyl] - 3
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Paragraph 0007; 0012-0015
(2017/08/30)
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- Method for synthesizing montrlukast sodium intermediate by means of series catalysis of graphene palladium cobalt
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The invention relates to a technology for chemical synthesis of a medicine intermediate, in particular to a method for synthesizing a montrlukast sodium intermediate-[S-(E)]-2-[3-[3-[2-(7-chlorine-2-quinolyl)vinyl]phenyl]-3-hydroxy propyl]methyl benzoate by means of series catalysis of graphene palladium cobalt. The method adopts two steps of coupling and reducing and a one-pot series catalytic system; the obtained intermediate product does not need to be separated; the method is simple in operation, high in yield and good in chiral selectivity, thus being suitable for industrial production.
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Paragraph 0007; 0013; 0014; 0015
(2017/08/30)
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- A process for the preparation of intermediates Menglusitena
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The invention discloses a preparation method of a montelukast sodium intermediate and belongs to the technical fields of pharmaceutical chemicals and biochemical engineering. The preparation method of the montelukast sodium intermediate comprises the foll
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Paragraph 0019; 0020
(2017/05/26)
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- BIARYL DIPHOSPHINE LIGANDS, INTERMEDIATES OF THE SAME AND THEIR USE IN ASYMMETRIC CATALYSIS
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The present disclosure relates to biaryl diphosphine ligands of the formula (B), processes for the production of the ligands and the use of the ligands in metal catalysts for asymmetric synthesis. The disclosure also relates to intermediates used for the production of the biaryl diphosphine ligand. (Formula (B))
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Page/Page column 58
(2012/03/27)
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- Identification, synthesis and characterization of impurities of Montelukast sodium
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Montelukast sodium is a selective leukotriene receptor antagonist which inhibits cysteinyl leukotriene CysLT1 receptor. Various synthesis of Montelukast is published. During laboratory optimization and later in bulk synthesis formation of various impurities was detected. Besides, pharma Europa draft mention nine process related impurities. However, the method of preparation of most of these impurities is not available in literature. Also, different route of synthesis will have different impurity profile and those process related impurities are not covered in pharmacopeias. In this study we report the synthesis of possible process impurities, including seven impurities (A-H) mentioned in pharma Europa.
- Sunil Kumar,Anjaneyulu,Hima Bindu
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scheme or table
p. 4536 - 4546
(2012/02/04)
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- AN IMPROVED PROCESS FOR THE PREPARATION OF MONTELUKAST SODIUM AND ITS INTERMEDIATES
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The present invention relates to a process for the preparation of montelukast sodium (formula 1) and formula 4. The invention concerns the coupling of thiol derivative, Methyl 1 - (mercaptomethyl)cyclopropane acetate with mesylate of formula 4 compound using alkyl substituted ammonium hydroxide base, alkali amides and purification of Montelukast acid by crystallization in suitable organic solvents. The invention further concerns to provide an improved process of montelukast intermediates having good yield and quality
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Page/Page column 5; 7; 11
(2010/06/20)
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- KETOREDUCTASE POLYPEPTIDES AND USES THEREOF
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The present disclosure provides engineered ketoreductase enzymes having improved properties as compared to a naturally occurring wild-type ketoreductase enzyme. Also provided are polynucleotides encoding the engineered ketoreductase enzymes, host cells capable of expressing the engineered ketoreductase enzymes, and methods of using the engineered ketoreductase enzymes to synthesize a variety of chiral compounds.
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- PROCESS FOR MAKING MONTELUKAST INTERMEDIATES
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A process for making a montelukast intermediate of formula (1) is achieved by reacting a compound of formula (2): with a hydrogen source in the presence of a ruthenium catalyst of formula (9): or a dimer thereof, wherein n represents a number from 1 to 3,
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Page/Page column 5
(2009/10/31)
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- SYNTHESIS OF LEUKOTRIENE COMPOUNDS
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The present invention relates to the synthesis of leukotriene receptor agonist compounds and to novel intermediates employed in their preparation. Leukotriene agonists are used in the treatment of asthma, as well as other conditions mediated by leukotrienes such as inflammation and allergies. A compound of particular interest is montelukast and the present invention describes an improved process for making montelukast and similar compounds.
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- PROCESS FOR THE PREPARATION OF MONTELUKAST, AND INTERMEDIATES THEREFOR
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The invention relates to processes for making montelukast and to intermediates for use in the process, in particular compounds of formulas 2-7: L=OAc, OTs, OTf5OMs; where X=Cl, Br, I.
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Page/Page column 17
(2008/06/13)
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- Process for the preparation of optically active ethenylphenyl-alcohols
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Optically active ethenylphenyl-alcohols of formula or its mirror image, wherein R1 is unsubstituted or substituted heteroaryl and R2 is phenyl or substituted aryl, are prepared by asymmetric hydrogenation of the corresponding ketones applying hydrogen gas in the presence of specific platinum metal complex catalysts.
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Page/Page column 10-11
(2008/12/08)
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- PROCESS
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A process of preparing montelukast, or a pharmaceutically acceptable salt thereof, which process comprises reacting a protected intermediate of formula (II) as defined in the specification with a cyclopropyl intermediate.
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Page/Page column 24
(2008/06/13)
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- PROCESS
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The present disclosure relates to an improved process for the preparation of enantiomerically enriched alcohols of Formula (I), from the corresponding ketone of Formula (II), by asymmetric transfer hydrogenation, using a hydrogen donor, catalyzed by a rut
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Page/Page column 11
(2008/06/13)
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- A PROCESS FOR SYNTHESIZING DIOL (VIII)-AN INTERMEDIATE OF MONTELUKAST SODIUM
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A process comprises preparing benzaldehyde of formula I in a conventional manner, reacting the said benzaldehyde I with Grignard reagent in water miscible etheral solvent to precipitate the alcohol of formula (II) by addition of ammonium salt and water followed by isolating the alcohol thus precipitated by any known methods and then oxidizing directly under "Swern's conditions" to get a ketone of formula m, enolizing the said ketone in presence of a mild base such as alkali metal alkoxide and then reacting it with dialkyl carbonate under conditions effective to yield a β- ketoester of formula IV, benzylating the said β-ketoester so obtained in the preceding step to form the benzoate of formula V in presence of mild inorganic base followed by decarboxylating the said benzoate to a mixture of a ketoester of formula VI and its corresponding acid of formula VIA in the presence of acidic conditions, alkylating the acid VIA present in the mixture in the preceding step to obtain ketoester of formula VI and purifying it if so desired, asymmetrically reducing the ketoester of formula VI, to a chiral alcohol of formula VII using (-) diisopinocamphenylchloroborane (-DIPC1) in presence of less than 4 times v/w aprotic solvent and optionally in presence of Lewis base with respect to the said ketoester of formula VI, treating the said chiral alcohol VII with cerium halo salt, and alkylmagnesium halide followed by isolating the title compound using hyflow supercel and ammonium chloride to get the intermediate diol of formula VIII. Atemately, the said alcohol to Heck coupling with methyl-2-iodobenzoate in presence of Lewis base, acetonitrile, and palladium acetate to yield ketoester (VI), which is converted to diol (VIII) as described herein above.
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Page/Page column 26-27
(2010/10/20)
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- The resolution of important pharmaceutical building blocks by palladium-catalyzed aerobic oxidation of secondary alcohols
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The palladium-catalyzed aerobic oxidative kinetic resolution of key pharmaceutical building blocks is described. Substrates investigated are relevant to the enantioselective preparation of Prozac, Singulair, and the promising hNK-1 receptor antagonist from Merck. The latter provides the most selective aerobic oxidative kinetic resolution yet described.
- Caspi, Daniel D.,Ebner, David C.,Bagdanoff, Jeffrey T.,Stoltz, Brian M.
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p. 185 - 189
(2007/10/03)
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- A convenient and economical method for the preparation of DIP-chloride(TM) and its application in the asymmetric reduction of aralkyl ketones
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A convenient and economical in situ preparation of DIP-chloride(TM) from NaBH4, BCl3 and α-pinene is described. Its application in the asymmetric reduction of representative aralkyl ketones is presented.
- Zhao, Mangzhu,King, Anthony O.,Larsen, Robert D.,Verhoeven, Thomas R.,Reider, Paul J.
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p. 2641 - 2644
(2007/10/03)
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