856258-53-2Relevant academic research and scientific papers
Synthesis of PPAR agonist via asymmetric hydrogenation of a cinnamic acid derivative and stereospecific displacement of (S)-2-chloropropionic acid
Houpis, Ioannis N.,Patterson, Lawrence E.,Alt, Charles A.,Rizzo, John R.,Zhang, Tony Y.,Haurez, Michael
, p. 1947 - 1950 (2007/10/03)
(Chemical Equation Presented) The synthesis of the peroxime proliferator activated receptor (PPAR) α,γ-agonist (1) was accomplished with high enantio- and diastereoselectivity by employing an asymmetric hydrogenation strategy, of an α-alkoxy cinnamic acid
Synthesis of a peroxime proliferator activated receptor (PPAR) α/γ agonist via stereocontrolled Williamson ether synthesis and stereospecific SN2 reaction of S-2-chloro propionic acid with phenoxides
Aikins, James A.,Haurez, Michael,Rizzo, John R.,Van Hoeck, Jean-Pierre,Brione, Willy,Kestemont, Jean-Paul,Stevens, Christophe,Lemair, Xavier,Stephenson, Gregory A.,Marlot, Eric,Forst, Mindy,Houpis, Ioannis N.
, p. 4695 - 4705 (2007/10/03)
The stereospecific synthesis of the PPAR α/γ agonist 1 was accomplished via ethylation of the optically pure trihydroxy derivative 6, itself derived via an enzymatic resolution. The ethylation can be accomplished without epimerization only under strict control of the reaction conditions and the choice of base (sodium tert-amylate), temperature (-30°C), order of addition, and solvent (DMF). The key diastereospecific SN2 reaction of the phenol 4 with S-2-chloropropionic acid is best achieved via the sodium phenoxide of 4 derived from Na0 as the reagent of choice. The structure elucidation and key purification protocols to achieve pharmaceutical purity will also be described
