163380-16-3

Basic information

• Product Name: (3’R)-Ezetimibe
• Synonyms: (3’R)-Ezetimibe;(3R,4S)-1-(4-Fluorophenyl)-3-[(3R)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone;EzetiMibe (3R)-IsoMer;(R)-EzetiMibe;(3R,4S)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one;Ezetimibe (3R,4S,3R)-Isome;Ezetimibe impurity 11;Ezetimibe Impurity K
• CAS NO: 163380-16-3
• Molecular Formula: C₂₄H₂₁F₂NO₃
• Molecular Weight: 409.4252464
• Product Categories: Aromatics;Drug Analogues;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 163380-16-3.mol
• Article Data: 10

Chemical Properties

• Melting Point: 129.5-132.5 °C
• 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: (3’R)-Ezetimibe(CAS DataBase Reference)
• NIST Chemistry Reference: (3’R)-Ezetimibe(163380-16-3)
• EPA Substance Registry System: (3’R)-Ezetimibe(163380-16-3)

Safety Data

• Hazardous Substances Data: 163380-16-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 163380-16-3 differently. You can refer to the following data:
1. Azetidinone Ezetimibe (E975000) analog
2. Azetidinone Ezetimibe (E975000) analog. A cholesterol absorption inhibitor.

Upstream product

• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 462-06-6 fluorobenzene 
• 108-55-4 glutaric anhydride, 
• 1017158-54-1 C₁₁H₁₃FO₃ 
• 1185883-41-3 (S)-3-(5-(4-fluorophenyl)-5,5-dimethoxypentanoyl)-4-phenyloxazolidin-2-one 
• 189028-93-1 (S)-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 
• 191330-56-0 [14C]-Sch 57871 
• 1593542-72-3 C₃₅H₄₃F₂NO₄Si 
• 1478663-95-4 (S)-3-((R)-2-((S)-(4-((tert-butyldimethylsilyl)oxy)phenyl)((4-fluorophenyl)amino)methyl)-4-(2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl)butanoyl)-4-phenyloxazolidin-2-one 
• 190595-65-4 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 
• 204589-80-0 methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate 

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.

Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe

An effective synthesis for syn-β-lactams was achieved using a Rh-catalyzed reductive Mannich-type reaction. A rhodium-hydride complex (Rh-H) derived from diethylzinc (Et2Zn) and a Rh catalyst was used for the 1,4-reduction of an α,β-unsaturated ester to give a Reformatsky-type reagent, which in turn, reacted with an imine to give the syn-β-lactam. Additionally, the reaction was applied to the synthesis of (±)-ezetimibe, a potent β-lactamic cholesterol absorption inhibitor.

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.