(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone

Product Name: (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone
CAS No.: 189028-93-1
Chemical Name: (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone
Synonyms: ZT-4;ETMB-04;uophenyL;Ezetimibe-27;]-4(S)-phenyL;API`sIntermediate;Ezetimibe Impurity 8;M-Fluoro oxazolidone;Ezetimibe Impuriry 32;Ezetimibe Impurity 41
CBNumber: CB2777355
Molecular Formula: C20H18FNO4
Formula Weight: 355.36
MOL File: 189028-93-1.mol

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(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone Property

Melting point:: 90.0 to 94.0 °C
Boiling point:: 568.4±50.0 °C(Predicted)
Density: 1.288±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
solubility: soluble in Acetone
form: powder to crystal
pka: -3.11±0.40(Predicted)
color: White to Light yellow
optical activity: Consistent with structure
InChI: InChI=1S/C20H18FNO4/c21-16-11-9-15(10-12-16)18(23)7-4-8-19(24)22-17(13-26-20(22)25)14-5-2-1-3-6-14/h1-3,5-6,9-12,17H,4,7-8,13H2/t17-/m1/s1
InChIKey: XXSSRSVXDNUAQX-QGZVFWFLSA-N
SMILES: C(C1=CC=C(F)C=C1)(=O)CCCC(N1[C@@H](C2=CC=CC=C2)COC1=O)=O
CAS DataBase Reference: 189028-93-1(CAS DataBase Reference)

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Safety

HS Code: 2934.99.4400

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical

Product number: P2111
Product name: (S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-2-oxazolidinone
Purity: >98.0%(HPLC)(N)
Packaging: 5g
Price: $70
Updated: 2025/07/31

TCI Chemical

Product number: P2111
Product name: (S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-2-oxazolidinone
Purity: >98.0%(HPLC)(N)
Packaging: 25g
Price: $279
Updated: 2025/07/31

TRC

Product number: D486425
Product name: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4(S)-phenyl-2-oxazolidinone
Packaging: 1g
Price: $745
Updated: 2021/12/16

TRC

Product number: D486425
Product name: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4(S)-phenyl-2-oxazolidinone
Packaging: 500mg
Price: $400
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FD22477
Product name: 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4S-phenyl-2-oxazolidinone
Packaging: 250g
Price: $600
Updated: 2021/12/16

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(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone Chemical Properties,Usage,Production

Chemical Properties

Off-White Solid

Uses

3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4(S)-phenyl-2-oxazolidinone (cas# 189028-93-1) is a compound useful in organic synthesis.

Application

(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone is a core chiral building block in the synthetic route of ezetimibe. Ezetimibe reduces blood cholesterol by inhibiting intestinal cholesterol absorption and is commonly used for the treatment of primary hypercholesterolemia and other related conditions. This intermediate is used to construct the key carbon chain and chiral center of the drug molecule. Through subsequent reactions such as condensation, reduction and cyclization, key groups including fluorophenyl and oxazolidinone are introduced, and finally the core structure of ezetimibe is formed via ring closure.

Synthesis

99395-88-7

149437-76-3

189028-93-1

Example 1: Preparation of ezetimibe; (1-1) Preparation of (4S)-3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone (Eq. 7); A reaction mixture was prepared by dissolving 200 g of 5-(4-fluorophenyl)-5-oxopentanoic acid (Eq. 8), 160 g of (S)-4-phenyl-oxazolidin-2-one (Eq. 9), and 11.6 g of 4- dimethylamino pyridine were dissolved in 600 mL of dichloromethane to prepare the reaction mixture. A solution prepared by dissolving 157 g of N,N'-dicyclohexylcarbimide in 200 mL of dichloromethane was added to the reaction mixture and stirred for 2 hours. Upon completion of the reaction, the resulting reaction mixture was filtered to remove the by-products. The filtrate was washed sequentially with 1 L of 6N HCl, 1 L of water and 1 L of saturated sodium chloride solution, dried with anhydrous magnesium sulfate, filtered and the solvent was removed by distillation under reduced pressure. The residue was dissolved in 2 L of methanol by heating and cooled to induce crystallization. 2L of water was added and stirred for 30 minutes. The solid was separated by filtration to give 289 g of (4S)-3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-2-oxazolidinone as a white solid (yield: 86%).1H NMR (300 MHz, CDCl3): δ 7.92 (2H, m), 7.35-7.13 (5H, m), 7.04 (2H, m). 5.43 (1H, q), 4.75 (1H, t), 4.22 (1H, q), 3.05-2.93 (4H, m), 2.03 (2H, m).

References

[1] Patent: WO2010/71358, 2010, A2. Location in patent: Page/Page column 14-15
[2] Patent: WO2006/122216, 2006, A2. Location in patent: Page/Page column 41-42
[3] Synthetic Communications, 2016, vol. 46, # 20, p. 1687 - 1693
[4] Patent: CN106397292, 2017, A. Location in patent: Paragraph 0053; 0086; 0087
[5] Patent: CN104513187, 2017, B. Location in patent: Paragraph 0063; 0064; 0065; 0066

(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone Preparation Products And Raw materials

Raw materials

Preparation Products

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(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone Suppliers

Canada 1 China 316 Germany 2 India 42 Japan 1 South Korea 1 Switzerland 1 United Kingdom 2 United States 17 USA 1 Global 384

Changzhou Huihan Biotechnology Co., Ltd.

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Heading （Nanjing）Pharmtechnologies Co., Ltd.

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Energy Chemical

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Beijing Ouhe Technology Co., Ltd

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View Lastest Price from (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone manufacturers

Jinan Ruitong Biotech Co., Ltd.

Product: 1-(4-Fluoro-phenyl)-5-(2-oxo-4-phenyl-oxazolidin-3-yl)-pentane-1,5-dione 189028-93-1
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 1
Release date: 2025-08-26

WUHAN FORTUNA CHEMICAL CO., LTD

Product: (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone 189028-93-1
Price: US $0.00-0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 1000kg
Release date: 2021-11-09

Shaanxi Dideu Medichem Co. Ltd

Product: (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone 189028-93-1
Price: US $1100.00/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 1T
Release date: 2020-07-06

189028-93-1, (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinoneRelated Search:

Ezetimibe Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate (3R,4S)-1-(4-Fluorophenyl)-2-oxo-4-[4-(benzyloxy)phenyl]-3-azetidinepropanoic acid PHENYL VALERATE TERT-AMYL METHYL ETHER Cyclopentanecarbaldehyde TETRAPENTYLAMMONIUM BROMIDE Oxadixyl EZETIMIBE-D4 1,5-Pentanedione, 1-(3-fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-3-oxazolidinyl]- PHENYL RESIN 4-(4-Fluorobenzoyl)butyric acid (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE 4-[[(4-Fluorophenyl)imino]methyl]-phenol 5-(4-FLUOROPHENYL)VALERIC ACID ent-EzetiMibe EzetiMibe (3R,4R,3'S)-IsoMer (R)-3-((S)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one

(4S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one

(S)-3-[5-(4-Fluorophenyl)-1,5-dioxopentyl]-4-phenyloxazolidin-2-one

1-(4-Fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-3-oxazolidinyl]-1,5-pentanedione

3-[5-(4-fluorophenyl)-1, 5-dioxopentyl]-4-phenyl-(4S)-2-Oxazolidinone (FHO2)

Ezetimibe Impurity 41

(S)-1-(4-fluorophenyl)-5- (2-oxo-4-phenyloxazolidin-3-yl) pentane-1,5-dione

ETMB-04

(S)-1-(4-fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)

1-(4-fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]pentane-1,5-dione

(S)-3-(5-(4-fluorophenyl)-5-oxopentanoyl)-4-phenyloxazolidin-2-one

(S)-3-(5-(4-fluorophenyl)-5-oxophentanoyl)-4-phenyloxazolidin-2-one

(S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-2-oxazolidinone

Ezetimibe Impurity 8

ZT-4

(S)-3-(4-(2-(4-fluorophenyl)-1,3-dioxolan-2-yl)butanoyl)-4-phenyloxazolidin-2-one

(<i>S</i>)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-2-oxazolidinone

(4s)-3-[5-(4-fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone

3-[5-[(4-FLUOROPHENYL)-1-5-DIOXOPENTA]-YL-4-(S)-PHENYL OXNZOLIDINE-2-ONE

3-[5-(4-FLUOROPHENYL)-1,5-DIOXOPENTYL]-4-PHENYL-(4S)-2-OXAZOLIDINONE

2-OXAZOLIDINONE, 3-[5-(4-FLUOROPHENYL)-1,5-DIOXOPENTYL]-4-PHENYL-, (4S)-

3-[5-(4-Fluorophenyl)-1,5-Dixopenyl]-4-Phenyl-(4s)-2-Oxazolidinone

(4S)-3-[5-(4-fluorophenyl)1,5-dioxophentyl]-4-phenyl-2-oxazolidinone

API`sIntermediate

(4S)-3-[5-(4-Fluorophenyl)-1,5-dixopenyl]-4-phenyl-2-oxazolidinone

2-OXAZOLIDINONE,3-[5-(4-FLUOROPHENYL)-1,5-DIOXOPENTYL]-4-PHENYL

E1:(4S)-3-[5-(4-fluorophenyl)1,5-dioxophentyl]-4-phenyl-2-oxazolidinone

Ezetimibe-27

Ezetimibe impuriry 26/(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone

(S)-1-(4-Fluorophenyl)-5-(2-oxo-4-phenyl-3-oxazolidinyl)-1,5-pentanedione

3-[5-(4-fluorophenyl)-5-oxopentanoyl]-4(S)-4-phenyl-1,3-oxazolidin-2-one

(S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-2-oxazolidinone&gt

Ezetimibe Intermediate Impurity T

]-4(S)-phenyL

3-[5-(1,5-Dioxo-5-(p-fL

uophenyL

1,5-Pentanedione, 1-(4-fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-3-oxazolidinyl]-

Etimibe intermediate 2

Ezetimibe Impuriry 32

1-(4-FLUOROPHENYL)-5-(2-OXO-4-PHENYLOXAZOLIDIN-3-YL)PENTANE-1,5-DIONE

(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazol

M-Fluoro oxazolidone

(4S) -3- [5- (4-fluorophenyl) -1,5-dioxapenyl] -4-phenyl-2-oxazolidinone

(S)-3-(5-(4-fluoropheny)-5-oxopentanoy)-4-phenyloxazolidin-2- one

Ezetimibe EP Impurity-C

(4S) -3- [5- (4-fluorophenyl) -1,5-dioxopentyl] -4-phenyl-2-oxazolidinone

Intermediate 2 of Etimibe

(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone, 99%min

(S)-1-(4-Fluorophenyl)-5-(2-oxo-4-phenyloxazolidin-3-yl)pentane-1,5-dione (Intermediate of Ezetimibe)

189028-93-1

Intermediate of ezetimibe

pharmaceutical

Ezetimibe intermediates

Aromatics