1593543-07-7

Basic information

• Product Name: (3S,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one
• Synonyms: (3S,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one;(3S,4S,3'S)-Ezetimibe;Ezetimibe Impurity A
• CAS NO: 1593543-07-7
• Molecular Formula: C24H21F2NO3
• Molecular Weight: 409.4252464
• Mol File: 1593543-07-7.mol
• Article Data: 78

Chemical Properties

• Boiling Point: 654.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.334±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.72±0.30(Predicted)
• CAS DataBase Reference: (3S,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(1593543-07-7)
• EPA Substance Registry System: (3S,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(1593543-07-7)

Safety Data

• Hazardous Substances Data: 1593543-07-7(Hazardous Substances Data)

Usage

Uses

(3S,4S,3’S)-Ezetimbe is a 3-epimer impurity of Ezetimibe (E975000), a cholesterol absorption inhibitor.

Upstream product

• 191330-56-0 [14C]-Sch 57871 
• 555-16-8 4-nitrobenzaldehdye 
• 371-40-4 4-fluoroaniline 
• 189028-95-3 (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one 
• 3489-09-6 4-fluoro-N-(4-nitrobenzylidene)aniline 
• 1354716-96-3 (4S)-phenyl-3-[(5S)-(4-fluorophenyl)-(2R)-[(1S)-(4-fluorophenylamino)-1-(4-nitrophenyl)methyl]-5-hydroxypentanoyl]oxazolidin-2-one 
• 1354716-98-5 (4S)-(4-aminophenyl)-1-(4-fluorophenyl)-(3R)-[(3S)-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one 
• 937798-07-7 C₂₆H₃₄FNO₄Si 
• 795306-57-9 3′-(S)-4-(S)-3-(R)-[3′-t-butyldimethylsilyloxy-3′-(4-fluorophenyl)propyl]-4-(4-hydroxyphenyl)-1-(4-fluorophenyl)azetidin-2-one 
• 163380-15-2 (3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one 
• 219653-96-0 (Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine 
• 204589-82-2 (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone 
• 204589-84-4 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride 
• 204589-80-0 methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 

Downstream Products

• 851860-30-5 (1S)-1-(4-fluorophenyl)-3-[(3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-{[(trifluoromethyl)sulfonyl]oxy}-phenyl)azetidin-3-yl]propyl acetate 
• 852204-12-7 (1S)-1-(4-fluorophenyl)-3-[(2S,3R)-1-(4-fluorophenyl)-2-(3'-hydroxybiphenyl-4-yl)-4-oxoazetidin-3-yl]propyl acetate 

Relevant articles and documents

Preparation method of ezetimibe and intermediate thereof

The invention discloses a preparation method of ezetimibe and an intermediate thereof. The invention provides a preparation method of an ezetimibe intermediate IV. The preparation method comprises thefollowing steps: an ezetimibe intermediate II and an ezetimibe intermediate III are subjected to a cyclization reaction to obtain the ezetimibe intermediate IV in the presence of a trialkylchlorosilane, an organic base, a chiral catalyst and lithium diisopropylamide in an organic solvent, wherein R is methyl, ethyl or propyl. The preparation method is short in route steps, mild in reaction conditions and simple in post-treatment steps, and avoids the connection of a substrate with a chiral group, and the obtained product is high in purity, achieves the standard of bulk drugs, is high in yield, low in production cost, high in atomic utilization rate, and suitable for industrial production.

Preparation method of ezetimibe SSS isomer

The invention relates to a preparation method of an ezetimibe SSS isomer. Specifically, the preparation method is used for producing the ezetimibe SSS cis-isomer by use of an RSS intermediate as a starting raw material and by virtue of Mitsunobu reaction and deprotection. The preparation method of the ezetimibe SSS isomer is simple in process steps, and the obtained product is good in yield and high in purity.

METHOD OF PREPARING EZETIMIBE AND INTERMEDIATE THEREOF

Disclosed is a method of preparing ezetimibe, including cross-metathesis using a Grubbs 2nd catalyst and deprotection using a Pearlman's catalyst, and an intermediate thereof. The method of preparing ezetimibe is useful as an efficient ezetimibe synthesis technique in pharmaceutical fields using ezetimibe as a raw material.