404874-93-7

Basic information

• Product Name: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone
• Synonyms: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone;(R)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione;1,5-Pentanedione, 1-(4-fluorophenyl)-5-[(4R)-2-oxo-4-phenyl-3-oxazolidinyl]-;Ezetimibe Impurity 8 Enantiomer
• CAS NO: 404874-93-7
• Molecular Formula: C20H18FNO4
• Molecular Weight: 355.3596232
• Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 404874-93-7.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Methanol (Sparingly)
• CAS DataBase Reference: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone(404874-93-7)
• EPA Substance Registry System: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone(404874-93-7)

Safety Data

• Hazardous Substances Data: 404874-93-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone is used in the preparation of ent-Ezetimibe (E975005) intermediates.

Upstream product

• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 149437-76-3 5-(4-fluorophenyl)-5-oxopentanoic acid 
• 1246853-48-4 (R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 528565-93-7 (4S)-3-[(5R)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 108-55-4 glutaric anhydride, 
• 462-06-6 fluorobenzene 
• 58518-77-7 ((1-(4-fluorophenyl)vinyl)oxy)trimethylsilane 
• 259529-54-9 (4S)-3-(1-oxo-2-propen-1-yl)-4-phenyl-1,3-oxazolidin-2-one 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 3282-30-2 pivaloyl chloride 
• 186343-35-1 (S)-5-phenyl-1,3-oxazolidine-2-one 
• 1056188-47-6 C₁₆H₁₉FO₄ 

Downstream Products

• 1246853-49-5 (R)-1-(4-fluorophenyl)-5-oxo-5-[(S)-2-oxo-4-phenyloxazolidin-3-yl]pentyl acetate 
• 1478664-18-4 (3S,4R)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1376614-99-1 (3S,4R)-1-(4-fluorophenyl)-3-((R)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 1376615-01-8 (3S,4R)-1-(4-fluorophenyl)-3-(3-(4-fluorophenyl)-3-oxopropyl)-4-(4-hydroxyphenyl)azetidin-2-one 
• 953805-22-6 3-{(2R,3S)-3-[(4-fluorophenyl)amino]-2-[2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl]-3-[4-(benzyloxy)phenyI]propanoyl}-(4S)-4-phenyl-1,3-oxazolidin-2-one 
• 953805-24-8 4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-3(R)-{2-[2-(4-fluorophenyI)-5,5-dimethyl-[1,3]-dioxan-2-yl]-ethyl}azetidine-2-one 
• 1004520-48-2 (3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azetidin-2-one 
• 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 
• 937798-07-7 C₂₆H₃₄FNO₄Si 

Relevant articles and documents

Ezetimibe intermediate and preparation method of ezetimibe

The invention relates to an ezetimibe intermediate and a preparation method of ezetimibe. The ezetimibe intermediate has a structure as represented by a formula (I). The preparation method comprises the following steps: providing a compound represented by a formula (II); subjecting the compound as shown in a formula (II) to an asymmetric catalytic hydrogenation reaction under the action of a P-BIAMH catalyst to prepare a compound shown as the formula (I), wherein the P-BIAMH catalyst has a structure as shown in a formula (A) which is described in the specification. In the formula (A), X and Yare halogen independently; R1 is H or a C1-9 alkyl group; R2 is a high-molecular polymer; and a fragment as described in the specification represents a diphosphorus ligand. The method has the advantages of high conversion rate and high safety, and is especially suitable for industrial production.

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.

Preparation method of ezetimibe intermediate

The invention discloses a preparation method of an ezetimibe intermediate. The intermediate is (S)-1-(4-fluorophenyl)-5-(2-oxo-phenyloxazolidinyl-3-yl)pentane-1, 5-dione. The preparation method comprises that 1-(4-fluorophenyl)ethanone and a silane protective agent undergo a reaction to produce ((1-(4-fluorophenyl)vinyl)oxo)trimethylsilane, (S)-4-phenyloxazolidin-2-one and acryloyl chloride undergo a condensation reaction to produce (S)-3-acrylyl-4-phenyloxazolidin-2-one, and the ((1-(4-fluorophenyl)vinyl)oxo)trimethylsilane and the (S)-3-acrylyl-4-phenyloxazolidin-2-one undergo a condensation reaction to produce the ezetimibe intermediate. The preparation method utilizes a convergent type route, has the total yield of 80% or more, utilizes cheap and easily available raw materials, utilizes less types of solvents, produces small toxicity, has a short production period, utilizes simple production units operated easily, is safe and environmentally friendly and is very suitable for industrial production.