1159183-24-0

Basic information

• Product Name: benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate
• Synonyms: benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate
• CAS NO: 1159183-24-0
• Molecular Weight: 543.567
• Mol File: 1159183-24-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate(1159183-24-0)
• EPA Substance Registry System: benzyl (4-((2S,3R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenyl) carbonate(1159183-24-0)

Safety Data

• Hazardous Substances Data: 1159183-24-0(Hazardous Substances Data)

Upstream product

• 1159183-23-9 C₃₂H₂₅F₂NO₅ 
• 501-53-1 benzyl chloroformate 
• 163222-33-1 ezetemibe 

Downstream Products

• 163222-33-1 ezetemibe 

Relevant articles and documents

Diastereoselective reduction of 1-(4-fluorophenyl)-3(R)-[3-oxo-3-(4- fluorophenyl)-propyl]-4(S)-(4-hydroxyphenyl)azetidin-2-one to Ezetimibe by the whole cell catalyst Rhodococcus fascians MO22

The asymmetric microbial reduction of 1-(4-fluorophenyl)-3(R)-[3-oxo-3-(4- fluorophenyl)-propyl]-4(S)-(4-hydroxyphenyl)azetidin-2-one to 1-(4-fluorophenyl)-3(R)-[3(S)-hydroxy-3-(4-fluorophenyl)-propyl]-4(S) -(4-hydroxyphenyl)azetidin-2-one (Ezetimibe) by Rhodococcus fascians MO22 is described. The catalytic capability of the microorganism for reduction has been examined also with protected ketone, an intermediate from chemical synthesis of Ezetimibe. Various parameters of the bioreduction have been optimized: the strain converted 94.8% of ketone and 63% of protected ketone into Ezetimibe with the same de of 99.9%. In the later case, two chemical steps are replaced with a single biotransformation.

A METHOD OF MANUFACTURING (3R,4S)-L-(4-FLUOROPHENYL)-3-[(3S)-3-(4-FLUOROPHENYL)-3- HYDROXYPROPYL)]-4-(4-HYDROXYPHENYL)-2-AZETIDINONE AND ITS INTERMEDIATES

A method of manufacturing (3R,4S)-l-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3- hydroxypropyl)]-4-(4-hydroxyphenyl)-2-azetidinone (ezetimibe) of formula I, in which a protected ketone of general formula II, wherein R stands for a protective group, such as benzyloxycarbonyl, tert-butoxycarbonyl, benzhydryl or trityl, is reduced with asymmetrical borane agents in an inert organic solvent in the temperature range of -30 to +40 °C, and finally the obtained protected alcohol of general formula III, wherein R has the same meaning as above, is deprotected by the action of hydro genolytic or acidic agents in an inert organic solvent.