(S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one
• CAS No.: 272778-12-8
• Molecular Formula: C39H46F2N2O5Si2
• Molecular Weight: 716.972
• European Community (EC) Number: 848-798-7
• UNII: MY62DF4M9J
• Mol file: 272778-12-8.mol

Synonyms:272778-12-8;(S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one;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;(4S)-3-[(2R,5S)-2-[(S)-(4-fluoroanilino)-(4-trimethylsilyloxyphenyl)methyl]-5-(4-fluorophenyl)-5-trimethylsilyloxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one;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)-;(4S3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl;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)-;Ezetimibe Impurity 9;MY62DF4M9J;C39H46F2N2O5Si2;SCHEMBL10045761;AMY19273;MFCD08460200;AKOS015896148;(4S)-3-[(2R,5S)-5-(4-FLUOROPHENYL)-2-[(S)-[(4-FLUOROPHENYL)AMINO][4-[(TRIMETHYLSILYL)OXY]PHENYL]METHYL]-1-OXO-5-[(TRIMETHYLSILYL)OXY]PENTYL]-4-PHENYL-2-OXAZOLIDINONE;(4S3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl]-1-oxo-5-[(trimethylsilyl)oxy]pentyl]-4-phenyl-2-oxazolidinone;DS-17844;CS-0158135;I11556;A818989;(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]-(4-trimethylsilyloxyphenyl)methyl]-5-trimethylsilyloxy-pentanoyl]-4-phenyl-1,3-oxazolidin-2-one;(s)-3-((2r,5s)-5-(4-fluorophenyl)-2-((s)-((4-fluorophenyl)amino)(4-((trimethyl silyl)oxy)phenyl)methyl)-5-((trimethyl silyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one;(S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-

Chemical Property of (S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one

Chemical Property:

• Vapor Pressure: 2.64E-22mmHg at 25°C
• Refractive Index: 1.565
• Boiling Point: 748.9 °C at 760 mmHg
• PKA: 3.55±0.50(Predicted)
• Flash Point: 406.7 °C
• PSA: 77.10000
• Density: 1.177 g/cm³
• LogP: 10.05190
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 14
• Exact Mass: 716.29133197
• Heavy Atom Count: 50
• Complexity: 1080

Purity/Quality:

99% ^*data from raw suppliers

(4R)-3-[(2S,5R)-5-(4-Fluorophenyl)-2-[(R)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl]-1-oxo-5-[(trimethylsilyl)oxy]pentyl]-4-phenyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)OC1=CC=C(C=C1)C(C(CCC(C2=CC=C(C=C2)F)O[Si](C)(C)C)C(=O)N3C(COC3=O)C4=CC=CC=C4)NC5=CC=C(C=C5)F
• Isomeric SMILES: C[Si](C)(C)OC1=CC=C(C=C1)[C@H]([C@@H](CC[C@@H](C2=CC=C(C=C2)F)O[Si](C)(C)C)C(=O)N3[C@H](COC3=O)C4=CC=CC=C4)NC5=CC=C(C=C5)F
• Uses: (4R)-3-[(2S,5R)-5-(4-Fluorophenyl)-2-[(R)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl]-1-oxo-5-[(trimethylsilyl)oxy]pentyl]-4-phenyl-2-oxazolidinone is an intermediate in the preparat ion of Ezetimibe (E975000). (4S3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]methyl]-1-oxo-5-[(trimethylsilyl)oxy]pentyl]-4-phenyl-2-oxazolidinone is used in the synthesis of Ezetimibe (E975000), an antihyperlipoproteinemic; a cholesterol absorption inhibitor.

Technology Process of (S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one

There total 3 articles about (S)-3-((2R,5S)-5-(4-Fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.6%

chloro-trimethyl-silane (75-77-4) + N-(4-hydroxybenzylidene)-4-fluorobenzenamine (3382-63-6,942485-62-3) + (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one (189028-95-3,528565-93-7) → (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 (272778-12-8)

Guidance literature:

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;

With titanium tetrachloride; In dichloromethane; at -30 - -25 ℃; Inert atmosphere;

Reference yield: 65.0%

chloro-trimethyl-silane (75-77-4) + (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one (189028-95-3,528565-93-7) → (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 (272778-12-8)

Guidance literature:

(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 ℃;

chloro-trimethyl-silane; In dichloromethane; at -5 ℃; for 1.5h;

With titanium tetrachloride; In dichloromethane; at -30 - -25 ℃; for 3h;

Reference yield: 60.0%

chloro-trimethyl-silane (75-77-4) + N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + N-(4-hydroxybenzylidene)-4-fluorobenzenamine (3382-63-6,942485-62-3) + (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidine-2-one (189028-95-3,528565-93-7) → (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 (272778-12-8)

Guidance literature:

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;

With titanium tetrachloride; In dichloromethane; at -30 ℃; for 20h;

N,O-bis-(trimethylsilyl)-acetamide;

upstream raw materials:

chloro-trimethyl-silane

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

N,O-bis-(trimethylsilyl)-acetamide

N-(4-hydroxybenzylidene)-4-fluorobenzenamine

Downstream raw materials:

ezetemibe

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

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