A practical synthesis for (S)-5-(4-(1-methylethoxy)phenyl)-5-methylimidazolidine-2,4-dione and its application in the synthesis of a novel liver X receptor β-selective agonist

Add time:09/07/2019    Source:sciencedirect.com

In this manuscript, the chiral separation of novel liver X receptor (LXR) β-selective agonist (±)-1 revealed that (S)-5-(4-(1-methylethoxy)phenyl)-5-methylimidazolidine-2,4-dione (+)-2 was the essential moiety (tail) to express LXR β-selective agonistic activity in a head-to-tail molecular design. The requisite configuration of (+)-2 was determined as the (S)-form by X-ray crystal structure analysis of (+)-halogenated 4. We obtained (S)-methyl 2-amino-2-(4-(1-methylethoxy)phenyl)propionate (+)-7 by resolution with l-mandelic acid and established a practical synthesis for (+)-2.

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