1376614-99-1

Basic information

• Product Name: ent-EzetiMibe
• Synonyms: ent-EzetiMibe;(3S,4R)-1-(4-Fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone;Ezetimibe Impurity 20;Ezetimibe Impurity C
• CAS NO: 1376614-99-1
• Molecular Formula: C₂₄H₂₁F₂NO₃
• Molecular Weight: 409.4252464
• Product Categories: Aromatics;Heterocycles;Impurities;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics, Heterocycles, Impurities, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1376614-99-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 654.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.334±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.72±0.30(Predicted)
• CAS DataBase Reference: ent-EzetiMibe(CAS DataBase Reference)
• NIST Chemistry Reference: ent-EzetiMibe(1376614-99-1)
• EPA Substance Registry System: ent-EzetiMibe(1376614-99-1)

Safety Data

• Hazardous Substances Data: 1376614-99-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An enantiomeric impurity of Ezetimibe (E975005).

Upstream product

• 1017158-54-1 C₁₁H₁₃FO₃ 
• 108-55-4 glutaric anhydride, 
• 462-06-6 fluorobenzene 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 404874-93-7 (R)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 
• 3382-63-6 (E)-(4-hydroxy-benzylidene)-(4-fluorophenyl)-amine 
• 371-40-4 4-fluoroaniline 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1376615-01-8 (3S,4R)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1593542-76-7 C₃₅H₄₃F₂NO₄Si 
• 1593542-67-6 C₄₄H₅₂F₂N₂O₆Si 
• 179411-51-9 N-(4-((tert-butyldimethylsilyl)oxy)benzylidene)-4-fluoroaniline 
• 953805-21-5 4-(2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl)butanoic acid 

Downstream Products

• 1376615-04-1 (3S,4R)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-(methoxyimino)propyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1376615-02-9 (3S,4R)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-(hydroxyimino)propyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1376615-01-8 (3S,4R)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl)azetidin-2-one 

Relevant articles and documents

Study on the HPLC-based separation of some ezetimibe stereoisomers and the underlying stereorecognition process

The enantioseparation of ezetimibe stereoisomers by high-performance liquid chromatography on different chiral stationary phases, ie, 3 polysaccharide-based chiral columns, was studied. It was observed that cellulose-based Chiralpak IC column exhibited the best resolving ability. After the optimization of mobile phase compositions in both normal and reversed phase modes, satisfactory separation could be obtained on Chiralpak IC column, especially in normal phase mode. The use of prohibited solvents as nonstandard mobile phase gave rise to better resolution than that of standard mobile phases (n-hexane/alcohol system). In addition, the presence of ethanol in nonstandard mobile phase has played an important role in enhancing chromatographic efficiency and resolution between ezetimibe stereoisomers. Various attempts were made to comprehensively compare the chiral recognition capabilities of immobilized versus coated polysaccharide-based chiral columns, amylose-based versus cellulose-based chiral stationary phases, reversed versus normal phase modes, and standard versus nonstandard mobile phases. Moreover, possible solute-mobile phase-stationary phase interactions were derived to explain how stationary and mobile phases affected the separation. Then the method validation with respect to selectivity, linearity, precision, accuracy, and robustness was carried out, which was demonstrated to be suitable and accurate for the quantitative determination of (RRS)-ezetimibe impurity in ezetimibe bulk drug.

First synthesis and characterization of key stereoisomers related to Ezetimibe

During the laboratory optimization and the late phase manufacturing studies of the cholesterol absorption inhibitor Ezetimibe 1, the formation of several stereoisomers was observed. To study the complete stereoisomer profile of Ezetimibe 1, we have synthesized and completely characterized several key stereoisomers of Ezetimibe 1 for the first time. This study will provide an access to the reference standard of these stereoisomers and may have some implications in the development of new medicines.