179 research outputs found
Synthese enantiomerenreiner DAVA-Derivate (5-Amino-4-hydroxypentansäuren) aus S-Glutaminsäure
Tofacitinib synthesis – An asymmetric challenge
co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265).
The authors would like to thank Hovione FarmaCiencia SA for financial support.Tofacitinib is a Janus activated kinase (JAK) inhibitor approved for the treatment of rheumatoid arthritis and active psoriatic arthritis. Its synthesis normally involves long synthetic sequences due to the chirality associated to the piperidine ring. This review is a comprehensive analysis of the different synthetic methods used to prepare this active pharmaceutical ingredient (API), covering the related journal and patent literature.authorsversionpublishe
Synthesis of 2S,5S- and 2R,5S-5-Hydroxypipecolic Acid via Amide-Methylenation of S-5-Hydroxy-2-piperidone with Dimethyltitanocene
A route to 2S,5S-and 2R,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselsctive methylenation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The transformation of the exocyclic enecarbamate double bond to the carboxylic acid group is best accomplished via hydroboration/oxidation to the alcohol 11a,b. Separation and oxidation of the dlastereomers 11a,b, to 148. and 14b, and hydrolysis furnishes the diastereomeric pipecolic acids 15a and 15b in enantiopure form
Aminosäuren, 4. Mitt. Die Oxidation vinyloger Aminoisocyanide mit Hg(II)-acetat zu Isocyanaten
ChemInform Abstract: Synthesis of (2S,4S,5S)-5-Hydroxy-4-methylpipecolic Acid (XIII) via Amide Methylenation of 5-Hydroxy-4-methyl-2-piperidinone with Dimethyltitanocene
ChemInform Abstract: Synthesis and Serotonin-Receptor Activity of Substituted 1-Oxo-1,2,3,4-tetrahydro-β-carbolines.
ChemInform Abstract: Synthesis of Homochiral Piperidine Derivatives from S-Glutamic Acid. Stereoselective 1,4-Addition of Organocuprates to a δ3-Piperidin- 2-one. A Paroxetine Analogue.
ChemInform Abstract: Enantiopure DAVA-Derivatives. Part 3. Synthesis of All Four Stereoisomers of 2-Methyl-4-hydroxy-5-aminopentanoic Acid (2-Me-4-OH- DAVA).
ChemInform Abstract: AMINO ACIDS. PART 4. OXIDATION OF VINYLOGOUS AMINOISOCYANIDES WITH MERCURY(II) ACETATE TO ISOCYANATES
ChemInform Abstract: Synthesis of Homochiral 3-Substituted Glutamic Acids and Prolines from Pyroglutamic Acid
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