1593543-00-0

Basic information

• Product Name: (3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one
• Synonyms: (3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one;(3S,4R,3'S)-Ezetimibe;Ezetimibe impurity 15;zetimibe (3S,4R,3'S)-Isomer;Ezetimibe Impurity E
• CAS NO: 1593543-00-0
• Molecular Formula: C24H21F2NO3
• Molecular Weight: 409.4252464
• Mol File: 1593543-00-0.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,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(1593543-00-0)
• EPA Substance Registry System: (3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one(1593543-00-0)

Safety Data

• Hazardous Substances Data: 1593543-00-0(Hazardous Substances Data)

Usage

Description

(3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one is a complex organic compound with a unique molecular structure. It is an enantiomeric impurity of Ezetimibe, which is a pharmaceutical drug used for treating hyperlipidemia and inhibiting cholesterol absorption.

Uses

Used in Pharmaceutical Industry:
(3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one is used as an enantiomeric impurity in the development and manufacturing process of Ezetimibe (E975005). This application is crucial for ensuring the purity, safety, and efficacy of the final drug product, as enantiomeric impurities can sometimes have different or even adverse effects on the body compared to the desired active ingredient.
In the pharmaceutical industry, the compound plays a vital role in the quality control and regulatory compliance of Ezetimibe, an antihyperlipidemic and cholesterol absorption inhibitor. By monitoring and controlling the presence of this specific enantiomeric impurity, manufacturers can ensure that the drug meets the required standards for therapeutic use and minimizes potential side effects or risks associated with impurities.

Upstream product

• 128376-64-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 942485-56-5 (S)-3-{4-[2-(4-fluorophenyl)dioxolan-2-yl]butanoyl}-4-phenyl-oxazolidin-2-one 
• 871366-43-7 C₁₉H₂₁BFNO₂ 
• 163380-15-2 (3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one 
• 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 
• 191330-56-0 [14C]-Sch 57871 
• 204589-80-0 methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 
• 219653-96-0 (Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine 
• 272778-13-9 (3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-(trimethylsilyloxy)propanyl)-4-(4-(trimethylsiloxy)phenyl)azetidinone 
• 231301-00-1 (3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one 
• 221349-60-6 (3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one 
• 221349-56-0 (3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one 
• 221349-58-2 (2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde 

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 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.