(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
(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)
Safety
- HS Code
- 2934.99.4400
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.
N-Bromosuccinimide Price
- 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
- 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
- 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
- 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
- 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
(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.
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
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View Lastest Price from (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone manufacturers
- 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
- 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
- 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