First synthesis and characterization of key stereoisomers related to Ezetimibe was written by Ren, Yun;Duan, Yan-Jun;Li, Ren-Jun;Deng, Yong;Hai, Li;Wu, Yong. And the article was included in Chinese Chemical Letters in 2014.Formula: C9H9NO2 This article mentions the following:
During a laboratory optimization and a late phase manufacturing study of the cholesterol absorption inhibitor ezetimibe, the formation of several stereoisomers was observed To study the complete stereoisomer profile of ezetimibe, the authors have synthesized and completely characterized several key stereoisomers of ezetimibe for the first time. This study will provide an access to the reference standard of these stereoisomers and may have some implications in the development of new medicines. The tilte compounds thus formed included (3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone (ezetimibe) and diastereomers, such as (3R,4R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone. The synthesis of the target compounds was achieved using 2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxane-2-butanoic acid and (4S)-4-phenyl-2-oxazolidinone and (4R)-4-phenyl-2-oxazolidinone (chiral auxiliary) as starting materials. Intermediates thus formed included (3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone and related diastereomers. In the experiment, the researchers used many compounds, for example, (S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7Formula: C9H9NO2).
(S)-4-Phenyloxazolidin-2-one (cas: 99395-88-7) belongs to oxazolidine derivatives. Oxazolidine-based compounds are well-known chiral auxiliaries and strategic molecular moieties in chemistry since they can effectively mask or mimic amino acid units or amino alcohols. In another report, the incorporation of an additional substituted oxazolidine ring over a range of new biphenylazepinium salt organocatalysts for the asymmetric epoxidation of alkenes improved enantiocontrol over the parent structures.Formula: C9H9NO2
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem