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

• 86217-38-1 4-phenyl-2-oxazolidinone 
• 60729-80-8 (S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid 
• 20989-17-7 (2S)-2-phenylglycinol 
• 105-58-8 Diethyl carbonate 
• 2935-35-5 (S)-2-phenylglycine 
• 503-38-8 trichloromethyl chloroformate 
• 616-38-6 carbonic acid dimethyl ester 
• 20989-17-7 Phenylglycinol 
• 67553-20-2 (+/-)-benzyl 2-hydroxy-1-phenylethylcarbamate 
• 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 
• 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 
• 52724-28-4 bis(tetraethylammonium) carbonate 
• 148766-15-8 (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one 
• 117049-14-6 tert-butyl N-[(1S)-2-hydroxy-1-phenylethyl]carbamate 

Downstream Products

• 150895-72-0 4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone 
• 111292-75-2 (4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one 
• 112530-18-4 (4S)-3-((2'R)-2'-methylbutanoyl)-4-phenyl-2-oxazolidinone 
• 112530-17-3 (4S)-3-((2'S)-2'-methylbutanoyl)-4-phenyl-2-oxazolidinone 
• 146137-31-7 (4S)-4-phenyl-3-<3-(4-methoxyphenyl)-2(E)-propenoyl>-2-oxazolidinone 
• 146137-36-2 (3(3S),4S)-4-phenyl-3-<3-(4'-methoxyphenyl)butanoyl>-2-oxazolidinone 
• 156721-19-6 (3(2E), 4S)-3-<3-(N-(2-mesitylenesulfonyl)-3-indolyl)-1-oxopropenyl>-4-phenyl-2-oxazolidinone 
• 99333-53-6 ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate 
• 148028-19-7 S 3-(1'-propene)-4-phenyl-2-oxazolidone 
• 141209-95-2 (4S)-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 146137-34-0 (4S)-4-phenyl-3-<(3S)-3-phenylbutyryl>oxazolidin-2-one 
• 146137-33-9 (4S)-4-phenyl-3-(3-phenylbutanoyl)oxazolidin-2-one 
• 154499-36-2 (4S)-3-(2-methyl-2-propenoyl)-4-phenyl-2-oxazolidinone 
• 184363-66-4 (4S)-4-benzyl-3-propionyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

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

The invention discloses a preparation method for synthesizing (S)-4-phenyl-2-oxazolidinone, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: reducing N-Boc-L-phenylglycine with a borane reagent to obtain N-Boc-L-phenylglycinol, and carrying out a ring closing reaction under the action of a catalyst to obtain (S)-4-phenyl-2-oxazolidinone. The product reacts with sulfur powder and ammonium sulfide or ammonium polysulfide to obtain (S)-4-phenyl oxazolidine-2-thioketone. The method avoids the use of cytotoxic reagents or solvents, has the advantages of accessible raw materials, simple operation and the like, conforms to green chemistry, and has potential industrial amplification prospects.

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.