1020157-01-0

Basic information

• Product Name: Trityl Olmesartan Medoxomil
• Synonyms: N2-Trityl OlMesartan MedoxoMil;(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(2-trityl-2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carboxylate;Olmesartan Medoxomil EP Impurity D;KKYFOXOGKNDKRS-UHFFFAOYSA-N
• CAS NO: 1020157-01-0
• Molecular Formula: C₄₈H₄₄N₆O₆
• Molecular Weight: 800.89956
• Mol File: 1020157-01-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 960.0±75.0 °C(Predicted)
• Appearance: /
• Density: 1.26±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methaniol (Slightly)
• PKA: 13.21±0.29(Predicted)
• CAS DataBase Reference: Trityl Olmesartan Medoxomil(CAS DataBase Reference)
• NIST Chemistry Reference: Trityl Olmesartan Medoxomil(1020157-01-0)
• EPA Substance Registry System: Trityl Olmesartan Medoxomil(1020157-01-0)

Safety Data

• Hazardous Substances Data: 1020157-01-0(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 133051-88-4 N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole 
• 80841-78-7 4-chloromethyl-5-methyl-1,3-dioxol-2-one 
• 144689-93-0 ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate 
• 172875-59-1 ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate 
• 124750-59-0 2-propyl-4,5-bis(methoxycarbonyl)-imidazole 
• 752179-89-8 1-((2'-(2-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid 
• 1048948-16-8 4-(1-hydroxy-1-methylethyl)-2-propyl-1-(4-(2-(trityltetrazol-5-yl)phenyl)phenylmethyl)-imidazole-5-carboxylic acid, sodium salt 
• 676-58-4 methylmagnesium chloride 
• 51802-42-7 2-propylimidazole-4,5-dicarbonitrile 
• 144689-94-1 diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate 
• 58954-23-7 2-propyl-1H-imidazole-4,5-dicarboxylic acid 

Downstream Products

• 144689-63-4 olmesartan 
• 144689-63-4 olmesartan medoxomil 

Relevant articles and documents

Development of efficient one-pot three-component assembly of trityl olmesartan medoxomil

We have elaborated a one-pot three-component assembly of trityl olmesartan medoxomil starting from commercially available ethyl 4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate, 5-(4′-(bromomethyl)-[1,1′-biphenyl]-2-yl)-1-trityl-1H-tetrazole and 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one intermediates. The developed and optimized one-pot process provides 72–75% yield of trityl olmesartan medoxomil over three steps, which represents in average ca. 90% yield per synthetic step, on a 300 g scale. The process is conducted in simple fashion and provides highly pure trityl olmesartan medoxomil (up to 97.5% by HPLC), which can be easily converted to olmesartan medoxomil that fully complies with all ICH requirements. Furthermore, the described process significantly improves the primary process to trityl olmesartan medoxomil by drastic reduction of required unit operations and application of single reaction solvent through the reaction sequence. Moreover, the amount of used organic solvents was notably reduced. The developed process has provided solid bases for industrial production of trityl olmesartan medoxomil.

METHOD FOR PRODUCING HIGH PURITY OLMESARTAN MEDOXOMIL

PROBLEM TO BE SOLVED: To provide a method for producing high purity olmesartan medoxomil. SOLUTION: There is provided a method for producing trityl olmesartan medoxomil which comprises: (a) a step of saponifying trityl olmesartan ethyl ester with a base in a water-soluble organic solvent; and (b) a step of reacting the product in the step a) and 4-chloromethyl-5-methyl-2-oxo-1,3-dioxolane in the presence of 0.5-fold more moles of an alkali metal iodide salt with respect to trityl olmesartan ethyl ester. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT

An improved process for the preparation of olmesartan medoxomil

Olmesartan medoxomil of high purity (99.3-99.7% by HPLC ) is prepared using an improved process of its intermediate, namely- ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-(2-(triphenylmethyl)-2H-tetrazol-5yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate, comprising: Reacting ethyl-4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate with N-(Triphenylmethyl)-5-[4'-(bromomethyl)biphenyl-2- yl]tetrazole in an organic solvent in presence of a base and a phase transfer catalyst in non-aqueous system to give after workup, ethyl-4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-[2-(triphenylmethyl)-2H-tetrazol-5yl]biphenyl-4-yl]methyl]imidazole-5-carboxylate, which is further processed, by following improved reaction conditions in three steps to provide substantially pure [HPLC purity 99.3 to 99.7 %] olmesartan medoxomil. A further process relates to the purification of olmesartan medoxomil by treatment with isopropyl alcohol and methyl ethyl ketone.