Determination of the Absolute Configuration and a Practical Chiral Synthesis of 5-[5-(1-Methylethoxy)pyridin-2-yl]-5-methyl­imidazolidine-2,4-dione as a Novel Liver X Receptor β-Selective Agonist

Autor:	Hisashi Sumida, Shigeru Ohba, Kimiyuki Shibuya, Minoru Koura
Rok vydání:	2017
Předmět:	Agonist Stereochemistry medicine.drug_class Organic Chemistry Hydrogen bromide Absolute configuration Enantioselective synthesis Hydantoin Mandelic acid Catalysis chemistry.chemical_compound chemistry Imidazolidine medicine Liver X receptor
Zdroj:	Synthesis. 49:2074-2080
ISSN:	1437-210X 0039-7881
Popis:	We determined that the absolute configuration of 5-[5-(1-methylethoxy)pyridin-2-yl]-5-methylimidazolidine-2,4-dione (hydantoin) is the (S)-form for the liver X receptor (LXR) β-selective agonist through X-ray crystal structure analysis of the hydantoin hydrogen bromide salt. Furthermore, we established a practical synthesis of the chiral hydantoin with 99% ee by the optical resolution of racemic methyl 2-amino-2-[5-(1-methylethoxy)pyridin-2-yl]propanoate with d -(–)-mandelic acid on a multi-kilogram scale. Finally, we improved the synthesis method of the LXR β-selective agonist.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::53a0cd9c34a97fcd7b4613896a4aab28 https://doi.org/10.1055/s-0036-1588700 Zobrazit plný text záznamu