343880-41-1Relevant academic research and scientific papers
A PROCESS FOR THE PREPARATION OF 3-ARYL-2-HYDROXY PROPANOIC ACID COMPOUNDS
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, (2014/12/09)
The present disclosure provides a process for synthesis of 3-aryl-2-hydroxy propanoic acid derivatives of formula (S)-1. wherein R1 represents H or (C1-C5) alkyl groups and R2 represents (C1-C5) alkyl groups.
A new enantioselective synthesis of (S)-2-ethoxy-3-(4-hydroxyphenyl) propanoic acid esters (EEHP and IEHP), useful pharmaceutical intermediates of PPAR agonists
Mujahid,Kunte,Muthukrishnan
, p. 3223 - 3226 (2014/06/09)
A new enantioselective synthetic route to the title compounds has been developed in a simple and practical way with high enantiopurity using commercially available starting material.
Biotechnological development of a practical synthesis of ethyl (S)-2-ethoxy-3-(p -methoxyphenyl)propanoate (EEHP): Over 100-fold productivity increase from yeast whole cells to recombinant isolated enzymes
Bechtold, Matthias,Brenna, Elisabetta,Femmer, Christian,Gatti, Francesco G.,Panke, Sven,Parmeggiani, Fabio,Sacchetti, Alessandro
experimental part, p. 269 - 276 (2012/08/07)
The coupling of the enantioselective reduction catalyzed by Old Yellow Enzymes (OYEs), together with the in situ substrate feeding product removal (SFPR) concept, significantly improved the productivity of the g-scale preparation of ethyl (S)-2-ethoxy-3-(p-methoxyphenyl)propanoate (EEHP), an important precursor of several PPAR-α/γ agonists, such as Tesaglitazar. The OYEs and the glucose dehydrogenase for cofactor regeneration were cloned, overexpressed in Escherichia coli, and purified. The synthetic sequence was completed by a NaClO2 oxidation employing cheap and environmentally friendly conditions. The product was obtained in 94% yield and with an ee of 98% over the two steps.
New stereospecific synthesis of Tesaglitazar and Navaglitazar precursors
Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Parmeggiani, Fabio
experimental part, p. 2694 - 2698 (2010/04/29)
A new synthetic route of to pharmaceutical intermediates (S)-1a-b and (S)-14 is reported. The reaction pathway is based on the baker's yeast-mediated reduction of the α-alkoxy cinnamaldehydes 9a-c to give the corresponding (S)-alcohols in good yields and
Enzyme-mediated synthesis of EEHP and EMHP, useful pharmaceutical intermediates of PPAR agonists
Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Parmeggiani, Fabio
experimental part, p. 2594 - 2599 (2010/03/30)
A new scaleable synthetic route to the title compounds has been developed. The reaction pathway is based on the α-chymotrypsin-catalysed hydrolysis of the racemic ethyl 2-ethoxy-3-(p-methoxyphenyl)propanoate or of the racemic ethyl 2-methoxy-3-(p-methoxyphenyl)propanoate to give the corresponding resolved (S)-esters with excellent ee. The acids were easily separated from the (S)-esters by a simple acid-base work-up. The overall yields of 1 and 2 were 16% and 17%, respectively.
Claisen condensation as a facile route to an α-alkoxy-cinnamate: Synthesis of ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate
Linderberg, Mats T.,Moge, Mikael,Sivadasan, Sivaprasad
, p. 838 - 845 (2013/09/03)
The title compound was prepared from p-anisaldehyde and ethyl ethoxyacetate via a racemic synthetic route. The synthesis involves a Claisen-type condensation in which the elimination was unexpectedly promoted by an excess of the ester. The process has been successfully performed on a 2000-L scale with a total yield over seven steps of 19%.
Crytalline form of (s)-2 ethoxy -3-[4-(2-{4- methanesulfonyloxyphenyl} ethoxy)phenyl]propanoic acid
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, (2008/06/13)
The present invention relates to a novel crystalline form of the compound (S)-2-ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl}ethoxy)phenyl]propanoic acid, shown by formula (I), or a pharmaceutically-acceptable salt thereof, and solvates thereof. The inventi
