99395-88-7

Basic information

• Product Name: (S)-(+)-4-Phenyl-2-oxazolidinone
• Synonyms: (S)-(+)-4-Phenyl-2-oxazolidinone,99%;(S)-(+)-4-Phenyl-2-o;(S)+4-PHENYL-2-OXAZOLDINONE;2-Oxazolidinone, 4-phenyl-, (S)-;S-POZ;(4S)-(+)-2-Oxo-4-phenyl-1,3-oxazolidine, [(4S)-(+)-2-Oxo-1,3-oxazolidin-4-yl]benzene;EzetiMibe IMpurity ((S)-4-Phenyloxazolidin-2-one);(S) - 4 - phenyl - 2 - pbo alkanes
• CAS NO: 99395-88-7
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 1312995-182-4
• Product Categories: chiral;Chiral Reagent;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Chiral chemicals;Peptide;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives;Oxazolidinone;Chiral Compounds
• Mol File: 99395-88-7.mol
• Article Data: 68

Chemical Properties

• Melting Point: 129-132 °C(lit.)
• Boiling Point: 290.25°C (rough estimate)
• Flash Point: 200 °C
• Appearance: White/Crystalline Powder
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 7.79E-07mmHg at 25°C
• Refractive Index: 72 ° (C=1, AcOEt)
• Storage Temp.: Store at 0-5°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.05±0.40(Predicted)
• BRN: 131918
• CAS DataBase Reference: (S)-(+)-4-Phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-4-Phenyl-2-oxazolidinone(99395-88-7)
• EPA Substance Registry System: (S)-(+)-4-Phenyl-2-oxazolidinone(99395-88-7)

Safety Data

• Hazard Codes: Xi,F+
• Statements: 12-36
• Safety Statements: 24/25-33-26-16-7/9
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 99395-88-7(Hazardous Substances Data)

Usage

Description

(S)-(+)-4-Phenyl-2-oxazolidinone is a white to light yellow crystalline powder that serves as a versatile chiral auxiliary for asymmetric synthesis. It is easily recyclable under mild conditions, which enhances its commercial potential. (S)-(+)-4-Phenyl-2-oxazolidinone is also an intermediate for the synthesis and development of cholesterol absorption inhibitors, such as AZD4121, and is used in the production of Ezetimibe.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-4-Phenyl-2-oxazolidinone is used as an intermediate for the synthesis and development of cholesterol absorption inhibitors, such as AZD4121. It plays a crucial role in the production of these medications, which help in managing cholesterol levels and reducing the risk of cardiovascular diseases.
Used in Drug Development:
(S)-(+)-4-Phenyl-2-oxazolidinone is used as an intermediate in the development of Ezetimibe, a drug that lowers bad cholesterol levels in the blood. (S)-(+)-4-Phenyl-2-oxazolidinone contributes to the creation of effective medications for the treatment of hypercholesterolemia and related conditions.
Used in Asymmetric Synthesis:
(S)-(+)-4-Phenyl-2-oxazolidinone is used as a versatile chiral auxiliary in asymmetric synthesis. Its ability to be easily recycled under mild conditions makes it a valuable component in the synthesis of various enantiomerically pure compounds, which are essential in the pharmaceutical, agrochemical, and fragrance industries.
For a recent review on the applications and potential of (S)-(+)-4-Phenyl-2-oxazolidinone, refer to Aldrichimica Acta.

InChI:InChI=1/C9H9NO2/c11-9-10-8(6-12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,10,11)/t8-/m1/s1

Upstream product

• 616-38-6 carbonic acid dimethyl ester 
• 20989-17-7 Phenylglycinol 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 97-72-3 2-Methylpropionic anhydride 
• 123-62-6 propionic acid anhydride 
• 591-51-5 phenyllithium 
• 124-38-9 carbon dioxide 
• 20989-17-7 (2S)-2-phenylglycinol 
• 148766-15-8 (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one 
• 52724-28-4 bis(tetraethylammonium) carbonate 
• 208391-45-1 (S)-3-{(2S,3R)-2-Azido-3-(4-tert-butyl-phenyl)-3-[3-(2-methoxy-ethoxymethoxy)-phenyl]-propionyl}-4-phenyl-oxazolidin-2-one 
• 208391-46-2 (S)-3-{(2S,3R)-2-Azido-3-biphenyl-4-yl-3-[3-(2-methoxy-ethoxymethoxy)-phenyl]-propionyl}-4-phenyl-oxazolidin-2-one 
• 67553-20-2 (+/-)-benzyl 2-hydroxy-1-phenylethylcarbamate 
• 2935-35-5 (S)-2-phenylglycine 

Downstream Products

• 111292-75-2 (4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one 
• 290369-84-5 (S)-3-((E)-3-Naphthalen-2-yl-acryloyl)-4-phenyl-oxazolidin-2-one 
• 192203-76-2 (4S)-3-(2-butynoyl)-4-phenyloxazolidin-2-one 
• 192203-79-5 (S)-4-Phenyl-3-(3-trimethylsilanyl-propynoyl)-oxazolidin-2-one 
• 192203-75-1 (4S)-3-(3-phenyl-2-propyonyl)-4-phenyloxazolidin-2-one 
• 157435-14-8 (S)-4-Phenyl-3-(5-phenyl-pentanoyl)-oxazolidin-2-one 
• 197020-74-9 (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine 
• 243121-07-5 (S)-3-[(E)-4,4,4-trifluorobut-2-enoyl]-4-phenyloxazolidin-2-one 
• 140372-83-4 (+)-(1R)-1-phenyl-2-(phenylthio)ethylamine 
• 478918-62-6 (Z)-4-phenyl-3-(2-phenylpropenyl)oxazolidin-2-one 
• 478918-63-7 (E)-4-phenyl-3-(2-phenylpropenyl)oxazolidin-2-one 
• 572923-05-8 4-phenyl-3-(p-tolyl)-oxazolidin-2-one 
• 666259-61-6 (4S)-3-[3-(5-methylindol-1-yl)propanoyl]-4-phenyl-1,3-oxazolidin-2-one 
• 316807-16-6 (7S,8S)-7-Nitro-8-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-nonanoic acid methyl ester 

Relevant articles and documents

Preparation method of S-4-phenyl-2-oxazolidinone

The invention discloses a preparation method of S-4-phenyl-2-azolidinone. The preparation method comprises the following steps: reducing a compound 8 by potassium borohydride under acidic conditions to obtain a compound 9, and cyclizing the compound 9 and diethyl carbonate under alkaline conditions to obtain a compound 10, thereby obtaining (s)-4-phenyl-2-azolidinone. The raw materials used in the preparation method are easy to obtain, the reaction conditions are mild, the steps are simple, flammable and explosive reagents are not used, and the preparation method is suitable for large-scale industrial production and high in safety; the reaction yield is higher, and the cost is lower. Wide application prospects are realized.

Preparation method of oxazolidinone compound

The preparation method comprises the following steps 1): dissolving aromatic amino acid in methanol, dissolving the aromatic amino acid in methanol, heating up to 50 - 60 °C heat preservation 1 - 2h, 2) reducing: adding a catalytic amount of lithium salt in ethanol water as a solvent. 3) Ring-closing: toluene is used as a solvent, a reduction product and diethyl carbonate are added to 100 °C, a sodium methoxide solution is added dropwise, and the product is obtained after completion of the dropwise addition and after-treatment and purification after completion of the normal pressure distillation to the temperature of 100 °C heat preservation. The lithium salt is introduced to participate in the reaction, sodium borohydride is selected as a solvent, sodium borohydride is completely dissolved, and the lithium salt can be free from the compound to improve the reaction activity, so that the use amount of sodium borohydride is reduced to 2 equivalent, and the production cost is remarkably reduced.

Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis

Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.