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189028-93-1

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Basic Information
CAS No.: 189028-93-1
Name: (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone
Article Data: 11
Cas Database
Molecular Structure:
Molecular Structure of 189028-93-1 ((4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone)
Formula: C20H18FNO4
Molecular Weight: 355.366
Synonyms: 2-Oxazolidinone,3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-, (4S)- (9CI);2-Oxazolidinone,3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-, (S)-;(S)-3-[4-(4-Fluorobenzoyl)-1-oxobutyl]-4-phenyloxazolidin-2-one;(S)-3-[5-(4-Fluorophenyl)-1,5-dioxopentyl]-4-phenyloxazolidin-2-one;
EINECS: 606-164-5
Density: 1.288 g/cm3
Melting Point: 90.0 to 94.0 °C
Boiling Point: 568.4 °C at 760 mmHg
Flash Point: 297.6 °C
PSA: 63.68000
LogP: 3.83670
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Synthetic route
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189028-93-1

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

Conditions
ConditionsYield
With iodine In toluene at 40℃;94%

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

189028-93-1

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

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 40℃; for 2h;91%
99395-88-7

(S)-4-phenyl-2-oxazolidinone

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5-(4-fluorophenyl)-5-oxopentanoic acid

189028-93-1

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

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane86%
Stage #1: 5-(4-fluorophenyl)-5-oxopentanoic acid With dmap; pivaloyl chloride In N,N-dimethyl-formamide at 2 - 20℃; for 1.5h;
Stage #2: (S)-4-phenyl-2-oxazolidinone In N,N-dimethyl-formamide at 30 - 35℃; for 2h;		85.7%
Stage #1: 5-(4-fluorophenyl)-5-oxopentanoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran at -10℃; for 4h; Evans Aldol Reaction; Inert atmosphere;
Stage #2: (S)-4-phenyl-2-oxazolidinone With lithium chloride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;		85%
3282-30-2

pivaloyl chloride

149437-76-3

5-(4-fluorophenyl)-5-oxopentanoic acid

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(S)-5-phenyl-1,3-oxazolidine-2-one

189028-93-1

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

Conditions
ConditionsYield
Stage #1: pivaloyl chloride; 5-(4-fluorophenyl)-5-oxopentanoic acid With dmap In N,N-dimethyl-formamide at 2 - 20℃; for 1.5h;
Stage #2: (S)-5-phenyl-1,3-oxazolidine-2-one With dmap In N,N-dimethyl-formamide at 30 - 35℃; for 2h;		85.7%
...Expand
1056188-47-6

C16H19FO4

99395-88-7

(S)-4-phenyl-2-oxazolidinone

189028-93-1

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

Conditions
ConditionsYield
Stage #1: C16H19FO4; (S)-4-phenyl-2-oxazolidinone With dmap In N,N-dimethyl-formamide for 7h; Heating / reflux;
Stage #2: With sulfuric acid In water; N,N-dimethyl-formamide for 0.5h;
Stage #3: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide
With dmap In DMF (N,N-dimethyl-formamide) for 7h; Heating / reflux;
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(S)-4-phenyl-2-oxazolidinone

189028-93-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chloro-trimethyl-silane / dichloromethane / 0.5 h / 0 - 10 °C
1.2: 2 h / 0 - 10 °C
1.3: 2 h / 0 - 20 °C
2.1: iodine / toluene / 40 °C
View Scheme

C24H26FNO5

189028-93-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme

C24H26FNO5

189028-93-1

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
2: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
3: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
1246853-48-4

(R,S)-3-[5-(4-fluorophenyl)-5-hydroxy-pentanoyl]-4-phenyl-oxazolidin-2-one

189028-93-1

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
2: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 4 h / 0 °C
2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 4 h / 0 °C
2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 4 h / 0 °C
2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 4 h / 0 °C
2: Candida rugosa lipase / di-isopropyl ether; aq. phosphate buffer / 120 h / 40 °C / Enzymatic reaction
3: Candida antarctica B lipase / toluene / 120 h / 35 °C / Enzymatic reaction
4: pyridinium chlorochromate / dichloromethane / 2 h / 40 °C
View Scheme
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1-(4-fluorophenyl)ethanone

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / N,N-dimethyl-formamide / 10 h / 100 °C / Inert atmosphere
2: iodine / toluene / 40 °C
View Scheme
Raw Materials
149437-76-3
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    Product name: (4S)-3-[5-(4-fluorophenyl)-1,5-Dioxopenyl]-4-Phenyl-2-Oxazolidinone CAS No.: 189028-93-1 Molecule Formula：C20H18FNO4 Molecule Weight：355.36 Purity: 99.0% Package: 25kg/drum Description：White powder Manufacture Standards：

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Chemistry

Molecular Structure of (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone (CAS NO.189028-93-1):

Molecular formula: C20H18FNO4
Molecular Weight: 355.36
H bond acceptors: 5
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 63.68Å2
Index of Refraction: 1.578
Molar Refractivity: 91.64 cm3
Molar Volume: 275.8 cm3
Surface Tension: 50.6 dyne/cm
Density: 1.288 g/cm3
Flash Point: 297.6 °C
Enthalpy of Vaporization: 85.3 kJ/mol
Boiling Point: 568.4 °C at 760 mmHg
Vapour Pressure: 6.19E-13 mmHg at 25°C
Product Categories: Intermediate of ezetimibe
SMILES: Fc1ccc(cc1)C(=O)CCCC(=O)N3C(=O)OC[C@@H]3c2ccccc2
InChI: InChI=1/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

Specification

  (4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone , with CAS number of 189028-93-1, can be called 2-Oxazolidinone,3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-, (4S)- (9CI) ; 2-Oxazolidinone,3-[5-(4-fluorophenyl)-1,5-dioxopentyl]-4-phenyl-, (S)- ; (4S)-4-Phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-1,3-oxazolidin-2-one ; (S)-3-[4-(4-Fluorobenzoyl)-1-oxobutyl]-4-phenyloxazolidin-2-one ; (S)-3-[5-(4-Fluorophenyl)-1,5-dioxopentyl]-4-phenyloxazolidin-2-one .