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

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
CAS No.: 272778-12-8
Chemical 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
Synonyms: ZT-6;]-oxy]phenyL;y)-oxy]pentyL;-(4S)-2-oxazoL;)-2-[(S)-[(4-fL;Ezetimibe INT 1;Ezetimibe inter-X;3-[(2R,5S)-5-(4-FL;Ezetimibe Impurity 9;Ezetimibe Impuriry 9
CBNumber: CB8482499
Molecular Formula: C39H46F2N2O5Si2
Formula Weight: 716.96
MOL File: 272778-12-8.mol

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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 Property

Melting point:: 190-200°C
Boiling point:: 748.9±60.0 °C(Predicted)
Density: 1.177
storage temp.: under inert gas (nitrogen or Argon) at 2–8 °C
solubility: Chloroform, Ethyl Acetate, Methanol
form: Solid
pka: 3.55±0.50(Predicted)
color: White to Off-White
InChIKey: XXMINDVVBVJXLN-GOFGAPPUSA-N
SMILES: O1C[C@H](C2=CC=CC=C2)N(C(=O)[C@@H]([C@H](NC2=CC=C(F)C=C2)C2=CC=C(O[Si](C)(C)C)C=C2)CC[C@@H](C2=CC=C(F)C=C2)O[Si](C)(C)C)C1=O
LogP: 10.28 at 21℃

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H413May cause long lasting harmful effects to aquatic life

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

TRC

Product number: F598440
Product name: (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
Packaging: 25mg
Price: $150
Updated: 2021/12/16

TRC

Product number: F598440
Product name: (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
Packaging: 250mg
Price: $1190
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 51437
Product name: (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
Packaging: 25mg
Price: $650
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: ORS0000643
Product name: 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)-
Purity: 95.00%
Packaging: 5G
Price: $909.56
Updated: 2021/12/16

Chemenu

Product number: CM137902
Product name: 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)-
Purity: 95%
Packaging: 5g
Price: $224
Updated: 2021/12/16

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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 Chemical Properties,Usage,Production

Chemical Properties

Off-white Solid

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).

Uses

(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.

Synthesis

75-77-4

189028-95-3

272778-12-8

Step (c): In a 500 ml three-necked round-bottomed flask, assemble a thermometer, dosing funnel and nitrogen inlet. To the flask was added a dichloromethane solution of Compound VIII (28.1 mmol as 10 g of Compound VIII) and Compound IX (12.05 g) from step (b), and the total volume of the reaction mixture was adjusted to 150 mL with dry dichloromethane.The mixture was cooled to -10 °C and N,N-diisopropylethylamine (DIPEA, 25.7 mL, 147.5 mmol), keeping the temperature at -10 °C. Subsequently, trimethylchlorosilane (3.4 mL, 30.8 mmol) was added slowly, keeping the reaction temperature at -10 °C. Stirring of the reaction mixture was continued for 2 hours. Upon completion of the reaction, the organic layer was separated and washed with 120 mL of water. The organic layer was concentrated to a smaller volume, bis(trimethylsilyl)acetamide (8.4 mL) was added and the mixture was heated to reflux for 30 minutes. The mixture was concentrated to remove the dichloromethane and the product was obtained by crystallization from a mixture of ethyl acetate and heptane. After filtration, washing and drying, 13 g of Compound III was obtained (65% yield based on Compound VIII).

References

[1] Patent: US2006/135755, 2006, A1. Location in patent: Page/Page column 16-17

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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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 Suppliers

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ZHENGZHOU JIUYI TIME NEW MATERIALS CO,.LTD

Product: 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 272778-12-8
Price: US $2.00-5.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2025-06-26

Sinoway Industrial co., ltd.

Product: 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 272778-12-8
Price: US $0.00-0.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 99% up, High Density
Supply Ability: 20 tons
Release date: 2024-06-27

Qiuxian Baitai New Material Co., LTD

Product: 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 272778-12-8
Price: US $10.00/KG
Min. Order: 1KG
Purity: 98%
Supply Ability: 500ton/Month
Release date: 2021-12-21

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-oxazolidinoneRelated Search:

ALTRENOGEST Acetaminophen Lithium bis(trimethylsilyl)amide Glycine N,N-Dimethyl-1,4-phenylenediamine EC 2.6.1.2 Trimethylphenylammonium chloride Betaine Dichloromethylphenylsilane Methyltriphenylphosphonium bromide 3-[5-(1,5-Dioxo-5-(p-fluophenylpentyl]-4R-phenyl-2-oxazolidinone EzetiMibe LactaM Cleaved Alcohol Ezetimibe 1,5-Pentanedione, 1,5-bis(4-fluorophenyl)- Tris(hydroxymethyl)aminomethane ent-EzetiMibe 5-(4-FLUOROPHENYL)VALERIC ACID EzetiMibe (3R,4R,3'S)-IsoMer

Ezetimibe Intermediate X

(4R)-3-[(2S,5R)-5-(4-Fluorophenyl)-2-[(R)-[(4-fluorophenyl)amino][4-[(trimethylsilyl)oxy]phenyl]meth

Ezetimibe inter-X

3-[(2R,5S)-5-(4-fluorophenyl)-2-{(S)-[4-fluorophenyl]Amino}[4-(trimethylsily)-oxy]pentyl]methyl-1-2oxo-5-(trimethylsilyl)-oxo]penyl]-4-phenyl-(4S)-2-oxazolidinon

E3:3-[(2R,5S)-5-(4-fluorophenyl)-2-{(S)-[(4-fluorophenyl)Amino]}[4-(trimethylsilyl)-oxy]pentyl]methyl-1-2oxo-5-( trimethylsilyl)-oxo]penyl]-4-phenyl-(4S)-2-oxazolidinone

(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

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)-

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

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)-

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)-2-Oxazolidinone

3-[(2R,5S)-5-(4-fluorophenyl)-2-{(S)-[4-fluorophenyl]Amino}[4-(trimethylsily)-oxy]pentyl]methyl-1-2oxo-5-(trimethylsilyl)-oxo]penyl]-4-phenyl-(4S)-2-oxazolidinone

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(INTERMEDIATE OF EZETIMIBE)

INTERMEDIATE OF EZETIMIBE

3-(2R,5S)-5-(4-fluorophenyl)-2-(S)-(4-fluorophenyl(amino)4-trimethylsilyl-oxyphenylmethyl-1-oxo-5-(trimethylsily)-oxypentyl-4-phenyl-(4S)-2-oxazolidinone

(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

Ezetimibe Impurity 9

ZT-6

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

(4S)-3-[(2R,5S)-5-(4-fluorophenyl)-2-[(S)-[(4-fluorophenyl)amino]-(4-trimethylsilyloxyphen yl)methyl]-5-trimethylsilyloxy-pentanoyl]-4-phenyl-1,3-oxazolidin-2-one

Ezetimibe Impurity 68

3-[2-[(4-fluoroanilino)-(4-trimethylsilyloxyphenyl)methyl]-5-(4-fluorophenyl)-1-oxo-5-trimethylsilyloxypentyl]-4-phenyl-2-oxazolidinone

-(4S)-2-oxazoL

(amino)]][4-[trimethyL

)-2-[(S)-[(4-fL

]-1-oxo-5-[(trimethyL

3-[(2R,5S)-5-(4-FL

y)-oxy]pentyL

]-oxy]phenyL

Ezetimibe INT 1

Ezetimibe Impurity 68 USP/EP/BP

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 USP/EP/BP

4S3-[(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

3-[(2R,5S)-5-(4-Fluorophenyl)-2-[(S)-[(4-fluorophenyl(amino)...

Ezetimibe Impuriry 9

3-[(2R,5S)-5-(4- fluorophenyl) -2-[(S)-[(4- fluorophenyl (amino) ]][4- (trimethylsilyl) oxy] phenyl] methyl ]-1- oxo -5-[ (trimethylsilyl) oxy] phenyl

{2-[3-(Fluorophenyl)-3-(trimethyl silyloxy)-propyl]-3-(4- fluoro phenyl amino) -3-(4-trimethyl silyloxy phenyl)-1- oxo-propyl}-4-(S) phenyl oxazolidin-2-one

Ezetimibe TMS intermediate

3-((2R,5S)-5-(4-fluorophenyl)-2-(S)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-1-((trimethylsilyl)oxy)pentyl)-4-phenyl-(4S)-2-oxazolidinone

3-{(2R,5S)-5-(4-Fluoro-phenyl)-2-[(S)-(4-fluoro-phenylamino)-(4-trimethylsilanyloxy-phenyl)-methyl]-5-trimethylsilanyloxy-pentanoyl}-4(S)-phenyl-oxazolidin-2-one

3- [(2R, 5S) -5- (4-fluorophenyl) -2- [(S) - [(4-fluorophenyl (amino) [4- (trimethylsilyl) oxygen] phenyl] methyl] -1-oxo-5- [(trimethylsilyl) oxygen] phenyl] -4-phenyl - (4S) -2-oxazolidinone

3- [(2R, 5S) -5- (4-fluorophenyl) -2- [(S) - [(4-fluorophenyl (amino) [4- (trimethylsiloxy) phenyl] methyl] -1-oxo-5- [(trimethylsiloxy) phenyl] -4-phenyl - (4S) -2-oxazolidinone

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, 99%min

(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 (Intermediate of Ezetimibe)

272778-12-8

C39H46F2N2O5Si2

Ezetimibe intermediates

Ezetimibe

pharmaceutical