528565-93-7

Basic information

• Product Name: (S)-3-((R)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one
• Synonyms: (S)-3-((R)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one;Ezetimibe Impurity 24;(3-[5-(4-Fluoro-phenyl)-5-(R)-hydroxy-pentanoyl]-4-(S)-phenyl-oxazolidin-2-one)
• CAS NO: 528565-93-7
• Molecular Formula: C20H20FNO4
• Molecular Weight: 357.3755032
• Mol File: 528565-93-7.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 572.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.297±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 14.17±0.20(Predicted)
• CAS DataBase Reference: (S)-3-((R)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-((R)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one(528565-93-7)
• EPA Substance Registry System: (S)-3-((R)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one(528565-93-7)

Safety Data

• Hazardous Substances Data: 528565-93-7(Hazardous Substances Data)

Usage

Uses

(S)-3-((R)-5-(4-Fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one is a key intermediate in the preparation of Ezetimibe for treating high cholesterol.

Upstream product

• 67-63-0 isopropyl alcohol 
• 189028-93-1 (S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione 
• 1246853-48-4 (R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 140-11-4 Benzyl acetate 
• 108-05-4 vinyl acetate 
• 1076200-08-2 3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 149437-67-2 5-(4-fluorophenyl)-5-oxopentanoic acid methyl ester 
• 108-55-4 glutaric anhydride, 
• 189028-94-2 (S)-5-(4-fluorophenyl)-5-hydroxypentanoic acid 
• 462-06-6 fluorobenzene 
• 793673-93-5 (-)-6-(4-fluorophenyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 795306-57-9 3′-(S)-4-(S)-3-(R)-[3′-t-butyldimethylsilyloxy-3′-(4-fluorophenyl)propyl]-4-(4-hydroxyphenyl)-1-(4-fluorophenyl)azetidin-2-one 

Relevant articles and documents

Synthesis method of cholesterol absorption selective inhibitor drug intermediate

The invention discloses a synthesis method of a cholesterol absorption selective inhibitor drug intermediate, and is characterized in that the synthesis method comprises the following steps of: dissolving a raw material ezetimibe intermediate (4S)-3-[5-(4-fluorophenyl)-1, 5-dioxopentyl]-4-phenyl-2-oxazolidinone in an organic solvent according to a proper proportion, adding a glucose aqueous solution into the system, rapidly stirring, adjusting the pH to a required value, adding enzyme and coenzyme to continue reaction, controlling the pH of the system in the reaction process until the reaction is finished, adjusting the pH to be acidic after the reaction is finished, extracting, washing with water, concentrating, and evaporating to dryness to remove the solvent, thereby obtaining an oily matter which is a target compound (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxyl valeryl]-4-phenyl-1, 3-oxazacyclopentane-2-ketone. The synthesis method of the cholesterol absorption selective inhibitor drug intermediate has the advantages of being environmentally friendly, high in yield and purity, simple in preparation process, high in economic profit and the like.

Crystal form of ezetimibe key intermediate and preparation method of crystal form

The invention provides a crystal form of an ezetimibe key intermediate and a preparation method of the crystal form. The invention relates to the crystal form of (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-2-oxazolidinone and a preparation method thereof. Specifically, the invention provides the crystal form of a compound represented as in a formula (1), and the characteristic diffraction peaks exist in an X-ray powder diffraction pattern at the following 2[theta] angles: 6.195+/-0.2 degrees, 7.640+/-0.2 degrees, 8.289+/-0.2 degrees, 12.847+/-0.2 degrees, 18.394+/-0.2 degrees,19.871+/-0.2 degrees, 21.548+/-0.2 degrees and 25.062+/-0.2 degrees.

according to folds Mai Bu and its intermediate synthesis method

The invention provides an Ezetimibe synthesis method comprising the following steps: (a) a compound (5) is subjected to asymmetric reduction reaction to obtain a compound (6), and the compound (6) and tert-butyldimethylsilyl chloride react in an organic solution under the action of alkali to obtain a compound (7); (b) the compound (7) and diisopropylethylamine are dissolved in the organic solution, titanium tetrachloride is added in the organic solution to react at 20-50 DEG C, and a compound (3) is added in the organic solution at minus 20 to minus 60 DEG C to react to obtain a compound (8); (c) the compound (8) and N,O-bis(trimethylsilyl) acetamide react in the organic solution at 20-80 DEG C, tetrabutylammonium fluoride trihydrate is added into the organic solution to react at 20-80 DEG C to obtain a compound (9); (d) the compound (9) is subjected to off-protection reaction to obtain Ezetimibe, wherein R is equal to TBS, Ac or COOCH2CCl3. The invention further provides an Ezetimibe intermediate and a preparation method thereof.