1185883-41-3

Basic information

• Product Name: (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one
• Synonyms: (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one
• CAS NO: 1185883-41-3
• Molecular Weight: 401.435
• Mol File: 1185883-41-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one(1185883-41-3)
• EPA Substance Registry System: (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one(1185883-41-3)

Safety Data

• Hazardous Substances Data: 1185883-41-3(Hazardous Substances Data)

Upstream product

• 189028-93-1 (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 
• 149-73-5 trimethyl orthoformate 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 

Downstream Products

• 1185883-42-4 C₄₁H₃₄F₂N₂O₇ 
• 163380-16-3 (3R,4S)-1-(4-fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-azetidin-2-one 
• 163222-33-1 ezetemibe 
• 191330-56-0 [14C]-Sch 57871 
• 1185883-38-8 C₄₁H₃₆F₂N₂O₇ 

Relevant articles and documents

Efficient and scalable process for the synthesis of antihypercholesterolemic drug ezetimibe

An efficient and scalable process for the synthesis of antihypercholesterolemic drug ezetimibe through chiral Evans auxiliary (S)-4-phenyl-2-oxazolidinone is described. The key steps in this process are the condensation of (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one and N-(4-((tert-butyldimethylsilyl)oxy)benzylidene)-4-fluoroaniline, and the stereoselective reduction of ezetimibe-ketone with NaBH4/I2, which is first applied in the synthesis of ezetimibe. The process is concise, mild, easy to operate, and highly stereoselective (99.6% of de value of ezetimibe). In addition, three diastereomers of ezetimibe are synthesized and served as the references in quality control of the product.

METHOD OF PRODUCING (3R,4S)-L-(4-FLUOROPHENYL)-3-[(3S)-3-(4-FLUOROPHENYL)- HYDROXYPROPYL)]-4-(4-HYDROXYPHENYL)-2-AZETIDINONE

Method of producing (3R,4S)-l-(4-fiuorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3- hydroxypropyl)]-4-(4-hydroxyphenyl)-2-azetidinone (ezetimibe) of formula I, in which alcohol-oxazolidide of general formula II, wherein PG is a phenol protecting group, such as a carbonate group, for instance benzyloxycarbonyl or tert-butyloxycarbonyl, or an arylmethyl group, for instance benzyl, benzhydryl or trityl, or a silyl group, for instance tert- butyldimethylsilyl or thexyldimethylsilyl, is silylated by silylation agents in an inert organic solvent in the temperature range of -10 0C to the boiling temperature of the mixture; the obtained silylether-oxazolidide of general formula III, wherein PG is as defined above and X is a silyl group of general formula SiR1R2R3, wherein R1 to R3 are identical or different alkyl groups with 1 to 5 carbon atoms or the phenyl group, is cyclized by action of bis(trimethylsilyl)acetamide and a base in an inert organic solvent in the temperature range of -20 to 40 0C; and, finally, the obtained protected azetidinone of general formula IV, wherein PG is as defined above and Y is hydrogen or the group X as defined above, is deprotected by action of deprotecting hydrogenolytic agents and/or acidic agents in an inert organic solvent.