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272778-12-8

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CAS No.: 272778-12-8
Name: 3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)]][4-[trimethylsilyl]-oxy]phenyl]methyl]-1-oxo-5-[(trimethylsily)-oxy]pentyl]-4-phenyl-(4S)-2-oxazolidinone
Article Data: 4
Molecular Structure:
Molecular Structure of 272778-12-8 (3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)]][4-[trimethylsilyl]-oxy]phenyl]methyl]-1-oxo-5-[(trimethylsily)-oxy]pentyl]-4-phenyl-(4S)-2-oxazolidinone)
Formula: C39H46F2N2O5Si2
Molecular Weight: 716.972
Synonyms: 2-Oxazolidinone,3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl]-1-oxo-5-[(trimethylsilyl)oxy]pentyl]-4-phenyl-,(4S)-;
EINECS: 1592732-453-0
Density: 1.177 g/cm3
Boiling Point: 748.9 °C at 760 mmHg
Flash Point: 406.7 °C
PSA: 77.10000
LogP: 10.05190
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Synthetic route
75-77-4

chloro-trimethyl-silane

3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

189028-95-3

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

272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 0℃; Inert atmosphere;
Stage #2: With titanium tetrachloride In dichloromethane at -30 - -25℃; Inert atmosphere;		66.6%
With triethylamine In dichloromethane at -20℃; Reagent/catalyst; Solvent;
...Expand
75-77-4

chloro-trimethyl-silane

189028-95-3

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

272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: (E)-(4-hydroxy-benzylidene)-(4-fluorophenyl)-amine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃;
Stage #2: chloro-trimethyl-silane In dichloromethane at -5℃; for 1.5h;
Stage #3: With titanium tetrachloride In dichloromethane at -30 - -25℃; for 3h;		65%
75-77-4

chloro-trimethyl-silane

10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

3382-63-6

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

189028-95-3

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

272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; N-(4-hydroxybenzylidene)-4-fluorobenzenamine; (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - -5℃; for 1h;
Stage #2: With titanium tetrachloride In dichloromethane at -30℃; for 20h;
Stage #3: N,O-bis-(trimethylsilyl)-acetamide		60%
...Expand
272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl)-3-(trimethylsilyloxy)propanyl)-4-(4-(trimethylsiloxy)phenyl)azetidinone

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutylammonium acetate In tert-butyl methyl ether at 20℃; for 0.25h; Product distribution / selectivity;
With N,O-bis-(trimethylsilyl)-acetamide; potassium acetate In tetrahydrofuran at 20 - 60℃; for 5.5h; Product distribution / selectivity;
Stage #1: (4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one With N,O-bis-(trimethylsilyl)-acetamide; potassium acetate In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: With tetrabutylammomium bromide In tetrahydrofuran at 20℃; for 0.7h; Product distribution / selectivity;
272778-12-8

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]({4-[(trimethylsilyl)oxy]phenyl})methyl]-5-[(trimethylsilyl)oxy]pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

163222-33-1

ezetemibe

Conditions
ConditionsYield
With N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride In toluene at 28℃; for 2.66667h; Temperature; Inert atmosphere; Large scale;
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Chemistry

Product Name: 3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)]][4-[trimethylsilyl]-oxy]phenyl]methyl]-1-oxo-5-[(trimethylsily)-oxy]pentyl]-4-phenyl-(4S)-2-oxazolidinone
Molecular Structure of 3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)]][4-[trimethylsilyl]-oxy]phenyl]methyl]-1-oxo-5-[(trimethylsily)-oxy]pentyl]-4-phenyl-(4S)-2-oxazolidinone (CAS NO.272778-12-8):

Molecular Formula: C39H48F2N2O4Si2
Molecular Weight: 702.98
CAS NO: 272778-12-8 
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 15
Polar Surface Area: 60.03 Å2
Index of Refraction: 1.558
Molar Refractivity: 198.56 cm3
Molar Volume: 615 cm3
Surface Tension: 39.5 dyne/cm
Density: 1.143 g/cm3
Flash Point: 405.7 °C
Enthalpy of Vaporization: 108.92 kJ/mol
Boiling Point: 747.2 °C at 760 mmHg
Vapour Pressure: 3.35E-22 mmHg at 25°C
Synonyms of 3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)]][4-[trimethylsilyl]-oxy]phenyl]methyl]-1-oxo-5-[(trimethylsily)-oxy]pentyl]-4-phenyl-(4S)-2-oxazolidinone (CAS NO.272778-12-8): 2-Oxazolidinone, 3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(s)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl]-1-oxo-5-[(trimethylsilyl)oxy]pentyl]-4-phenyl-, (4S)- 
SMILES: C[Si](C)(C)Oc1ccc(cc1)[C@H]([C@@H](CC[C@@H](c2ccc(cc2)F)O[Si](C)(C)C)CN3[C@H](COC3=O)c4ccccc4)Nc5ccc(cc5)F 
InChI: InChI=1/C39H48F2N2O4Si2/c1-48(2,3)46-35-23-14-30(15-24-35)38(42-34-21-19-33(41)20-22-34)31(26-43-36(27-45-39(43)44)28-10-8-7-9-11-28)16-25-37(47-49(4,5)6)29-12-17-32(40)18-13-29/h7-15,17-24,31,36-38,42H,16,25-27H2,1-6H3/t31-,36+,37-,38+/m0/s1
InChIKey: IUUHLCBMXXGIDB-AUUUEPFHBQ
Std. InChI: InChI=1S/C39H48F2N2O4Si2/c1-48(2,3)46-35-23-14-30(15-24-35)38(42-34-21-19-33(41)20-22-34)31(26-43-36(27-45-39(43)44)28-10-8-7-9-11-28)16-25-37(47-49(4,5)6)29-12-17-32(40)18-13-29/h7-15,17-24,31,36-38,42H,16,25-27H2,1-6H3/t31-,36+,37-,38+/m0/s1 
Std. InChIKey: IUUHLCBMXXGIDB-AUUUEPFHSA-N

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