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

Minoru Koura, Hisashi Sumida, Kimiyuki Shibuya, Shigeru Ohba

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
JournalSynthesis (Germany)
DOIs
Publication statusAccepted/In press - 2017 Jan 13

Keywords

  • chiral synthesis
  • d-(–)-mandelic acid
  • hydantoin
  • liver X receptor
  • optical resolution
  • X-ray crystal structure analysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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