7152-04-7Relevant academic research and scientific papers
Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation
Hardegger, Leo A.,Humair, Roger,Sidler, Eric
, p. 1756 - 1762 (2020/10/26)
During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.
Ultrastrong, Transparent Polytruxillamides Derived from Microbial Photodimers
Tateyama, Seiji,Masuo, Shunsuke,Suvannasara, Phruetchika,Oka, Yuuki,Miyazato, Akio,Yasaki, Katsuaki,Teerawatananond, Thapong,Muangsin, Nongnuj,Zhou, Shengmin,Kawasaki, Yukie,Zhu, Longbao,Zhou, Zhemin,Takaya, Naoki,Kaneko, Tatsuo
, p. 3336 - 3342 (2016/06/01)
Ultrastrong and transparent bioplastics are generated from fermented microbial monomers. An exotic aromatic amino acid, 4-aminocinnamic acid, was prepared from a biomass using recombinant bacteria, and quantitatively photodimerized, and diacid and diamino monomers that were both characterized by a rigid α-truxillate structure were generated. These two monomers were polycondensed to create the polyamides with a phenylenecyclobutane repeating backbone such as poly{(4,4′-diyl-α-truxillic acid dimethyl ester) 4,4′-diacetamido-α-truxillamide} which was processed into amorphous fibers and plastic films having high transparency. In spite of noncrystalline structure, mechanical strength of the fiber is 407 MPa at maximum higher than those of other transparent plastics and borosilicate glasses, presumably due to the tentative molecular spring function of the phenylenecyclobutanyl backbone.
POLYMER RAW MATERIAL AND POLYMER MATERIAL
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Paragraph 0078; 0079; 0080; 0081, (2014/11/11)
To provide a polymer material having properties that allow the polymer material to replace a polyimide and a polyamide synthesized from a petroleum raw material, said polymer material being synthesized from a raw material derived from natural molecules. [
