(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone Chemical Properties

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 Information

HS Code 

2934.99.4400

(4S)-3-[5-(4-Fluorophenyl)-1,5-dioxopenyl]-4-phenyl-2-oxazolidinone Usage And Synthesis

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

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(189028-93-1)Related Product Information

• Ezetimibe
• Methyl (3R,4S)-1-(4-fluorophenyl)-2-oxo-4-[4-(phenylmethoxy)phenyl]-3-azetidinepropanoate
• (3R,4S)-1-(4-Fluorophenyl)-2-oxo-4-[4-(benzyloxy)phenyl]-3-azetidinepropanoic acid
• PHENYL VALERATE
• TERT-AMYL METHYL ETHER
• Cyclopentanecarbaldehyde
• TETRAPENTYLAMMONIUM BROMIDE
• Oxadixyl
• EZETIMIBE-D4
• 1,5-Pentanedione, 1-(3-fluorophenyl)-5-[(4S)-2-oxo-4-phenyl-3-oxazolidinyl]-
• PHENYL RESIN
• 4-(4-Fluorobenzoyl)butyric acid
• (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE
• 4-[[(4-Fluorophenyl)imino]methyl]-phenol
• 5-(4-FLUOROPHENYL)VALERIC ACID
• ent-EzetiMibe
• EzetiMibe (3R,4R,3'S)-IsoMer
• (R)-3-((S)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one