1296129-15-1

Basic information

• Product Name: (2R,3R,6S)-N,6-Bis(4-fluorophenyl)tetrahydro-2-(4-hydroxyphenyl)-2H-pyran-3-carboxaMide
• Synonyms: (2R,3R,6S)-N,6-Bis(4-fluorophenyl)tetrahydro-2-(4-hydroxyphenyl)-2H-pyran-3-carboxaMide;EzetiMibe Tetrahydropyran IMpurity;EzetiMibe Tetrahydropyran IMpurity (SCH59566);(2R,3R,6S)-N,6-bis(4-fluorophenyl)-2-(4-hydroxyphenyl)tetrahydro-2H-pyran-3-carboxaMide;EZT cyclic ether;Ezetimibe Impurity 17(SCH59566)
• CAS NO: 1296129-15-1
• Molecular Formula: C₂₄H₂₁F₂NO₃
• Molecular Weight: 409.4252464
• Product Categories: Amines;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 1296129-15-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 626.7±55.0 °C(Predicted)
• Appearance: /
• Density: 1.315±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.89±0.30(Predicted)
• CAS DataBase Reference: (2R,3R,6S)-N,6-Bis(4-fluorophenyl)tetrahydro-2-(4-hydroxyphenyl)-2H-pyran-3-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,6S)-N,6-Bis(4-fluorophenyl)tetrahydro-2-(4-hydroxyphenyl)-2H-pyran-3-carboxaMide(1296129-15-1)
• EPA Substance Registry System: (2R,3R,6S)-N,6-Bis(4-fluorophenyl)tetrahydro-2-(4-hydroxyphenyl)-2H-pyran-3-carboxaMide(1296129-15-1)

Safety Data

• Hazardous Substances Data: 1296129-15-1(Hazardous Substances Data)

Usage

Uses

Ezetimibe (E975000) tetrahydropyran impurity.

Upstream product

• 163222-33-1 ezetemibe 

Relevant articles and documents

Kinetics and mechanism of the base-catalyzed rearrangement and hydrolysis of ezetimibe

The pH-rate profile of the pseudo-first-order rate constants for the rearrangement and hydrolysis of Ezetimibe giving (2R,3R,6S)-N,6-bis(4- fluorophenyl)-2-(4-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-3-carboxamide (2) as the main product at pH of less than 12.5 and the mixture of 2 and 5-(4-fluorophenyl)-5-hydroxy-2-[(4-fluorophenylamino)-(4-hydroxyphenyl)methyl] -pentanoic acid (3) at pH of more than 12.5 in aqueous tertiary amine buffers and in sodium hydroxide solutions at ionic strength I = 0.1 mol L-1 (KCl) and at 39C is reported. No buffer catalysis was observed and only specific base catalysis is involved. The pH-rate profile is more complex than the pH-rate profiles for the hydrolysis of simple β-lactams and it contains several breaks. Up to pH 9, the log kobs linearly increases with pH, but between pH 9 and 11 a distinct break downwards occurs and the values of log kobs slightly decrease with increasing pH of the medium. At pH of approximately 13, another break upwards occurs that corresponds to the formation of compound 3 that is slowly converted to (2R,3R,6S)-6-(4-fluorophenyl)-2-(4- hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-3-carboxylic acid (4). The kinetics of base-catalyzed hydrolysis of structurally similar azetidinone is also discussed. 2014 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 103:2240-2247, 2014