204589-80-0

Basic information

• Product Name: Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate
• Synonyms: Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate;3-Azetidinepropanoic acid, 1-(4-fluorophenyl)-2-oxo-4-[4-(phenylMethoxy)phenyl]-, Methyl ester, (3R,4S)- (REACH);3-Azetidinepropanoic acid, 1-(4-fluorophenyl)-2-oxo-4-[4-(phenylMethoxy)phenyl]-, Methyl ester, (3R,4S)-;1-(4-fluorophenyl)-2-oxo-4-[4-(phenylMethoxy)phenyl]-,Methyl ester,(3R,4S)-3-Azetidinepropanoic acid;Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate;Trans-methyl-3-(((3-[2-oxo-4(benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinone])propionate;Ezetimibe Impurity 18
• CAS NO: 204589-80-0
• Molecular Formula: C₂₆H₂₄FNO₄
• Molecular Weight: 433.47
• EINECS: 1308068-626-2
• Mol File: 204589-80-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 628.309 °C at 760 mmHg
• Flash Point: 333.789 °C
• Appearance: /
• Density: 1.238
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.589
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate(204589-80-0)
• EPA Substance Registry System: Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate(204589-80-0)

Safety Data

• Hazardous Substances Data: 204589-80-0(Hazardous Substances Data)

Usage

Uses

Methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate is a reagent for the synthesis of antihypercholesterolemia drug ezetimibe.

InChI:InChI=1/C26H24FNO4/c1-31-24(29)16-15-23-25(28(26(23)30)21-11-9-20(27)10-12-21)19-7-13-22(14-8-19)32-17-18-5-3-2-4-6-18/h2-14,23,25H,15-17H2,1H3/t23-,25-/m1/s1

Upstream product

• 934245-17-7 3-[2-(3-methoxy-3-oxopropyl)-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxopropyl]-4(S)-phenyloxazolidin-2-one 
• 204589-82-2 (3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1412967-14-6 (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one 
• 917392-16-6 N-{2-[3-(methoxy)-3-(oxo)-propyl]-3-(4-fluorophenylamino)-3-(4-benzyloxyphenyl)-1-oxo-propyl}-4-(S)-phenyloxazolidin-2-one 
• 1501-26-4 methyl 4-(chlorocarbonyl)butyrate 
• 219653-96-0 (Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine 

Downstream Products

• 190595-65-4 (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one 
• 1412967-14-6 (3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one 
• 934245-14-4 3-[(2S,3R)-2-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-N-methoxy-N-methylpropaneamide 
• 1042722-99-5 methyl 3-[(2S,3R)-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)-4-oxoazetidin-3-yl]propionate 

Relevant articles and documents

Formal Synthesis of Ezetimibe Using a Proline-mediated, Asymmetric, Three-component Mannich Reaction

The formal total synthesis of ezetimibe was accomplished using a proline-mediated, asymmetric, three-component Mannich reaction as the key step. The two stereogenic centers on the β-lactam skeleton of ezetimibe were controlled by the syn-selective asymmetric Mannich reaction, followed by isomerization.

IMPROVED PROCESS FOR THE PREPARATION OF EZETIMIBE AND ITS INTERMEDIATES

The present invention provides an improved process for the preparation of ezetimibe through novel organic amine salt compounds of general formula (1). The present invention also relates to a highly pure ezetimibe and 3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl) azetidin-3-yl)propionic acid compound.

IMPROVED PROCESS FOR THE PREPARATION OF EZETIMIBE

The present invention relates to a cost effective and industrially advantageous process for the preparation of (3R,4S)-l-(4-Fluorophenyl)-3-[3(S)-3-(4-fluorophenyl)-3 - hydroxypropyl)]-4-(4-hydroxyρhenyl)-2-azetidinone, referred to here as Ezetimibe, it is represented as formula (1).