(4S)-3-[(5R)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

(4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1, 3-OXAZOLIDIN-2-ONE is a derivative of 2-oxazolidine, which is an effective antimicrobial. It can be used as a pharmaceutical intermediate for the preparation of ezetimibe which is a drug used to lower the patients’ plasma cholesterol levels.

Solid

3-[(5S)-(4-Fluorophenyl)-5-hydroxypentanoyl]-(4S)-phenyl-1,3-oxazolidin-2-one is an intermediate of Ezetimibe (E975000, E975002), an antihyperlipoproteinemic. A cholesterol absorption inhibitor.

A process for synthesis of (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE comprising of resolution of 4S- phenyl -3-[(5RS)-5-(4-fluorophenyl)-5-hydroxypentanoyl] -1,3 oxazolidin 2-one by selective esterification of 4S-phenyl -3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl] -1,3 oxazolidin 2-one using appropriate esterification reagent in an organic solvent in presence of Lipase enzyme at a temperature ranging from 0° to 100°C, and further isolation.

http://www.cphi-online.com/ezetimibe-intermediate-4s3-prod587443.html
https://en.wikipedia.org/wiki/2-Oxazolidone