1478664-18-4

Basic information

• Product Name: (3S,4S)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one
• Synonyms: (3S,4S)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one;(3S,4S,3'R)-Ezetimibe;Ezetimibe Impurity 29
• CAS NO: 1478664-18-4
• Molecular Formula: C24H21F2NO3
• Molecular Weight: 409.4252464
• Mol File: 1478664-18-4.mol
• Article Data: 78

Chemical Properties

• Boiling Point: 654.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.334±0.06 g/cm3(Predicted)
• PKA: 9.72±0.30(Predicted)
• CAS DataBase Reference: (3S,4S)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(1478664-18-4)
• EPA Substance Registry System: (3S,4S)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(1478664-18-4)

Safety Data

• Hazardous Substances Data: 1478664-18-4(Hazardous Substances Data)

Usage

Uses

(3S,4S,3''R)-Ezetimibe is derived from (3S,4S)-1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]-4-(4-hydroxyphenyl)-2-azetidinone (F595055), which is an intermediate in the synthesis of (3S,4S,3’S)-Ezetimbe (E975040), which is a 3-epimer impurity of Ezetimibe (E975000), a cholesterol absorption inhibitor.

Upstream product

• 873205-85-7 1-(4-fluorophenyl)-3(R)-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4(S)-(4-hydroxyphenyl)-2-azetidinone hydrate 
• 190595-65-4 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 
• 1004520-48-2 (3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azetidin-2-one 
• 272778-12-8 (4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 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 
• 191330-56-0 [14C]-Sch 57871 

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 

Relevant articles and documents

Preparation method of ezetimibe optical isomer

The invention relates to a preparation method of an ezetimibe optical isomer, and concretely relates to a method for synthesizing an ezetimibe impurity L by using a compound 03. The method comprises the following steps: 1) mixing the compound 03 with a silyl ether protecting group, 2) adding methyl tert-butyl ether, and 3) adding alcohol and acid.

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.