17097-67-5

Basic information

• Product Name: (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone
• Synonyms: (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone;(4S-trans)-4-Methyl-5-phenyl-2-oxazolidinone
• CAS NO: 17097-67-5
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.19984
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 17097-67-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone(17097-67-5)
• EPA Substance Registry System: (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone(17097-67-5)

Safety Data

• Hazardous Substances Data: 17097-67-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone is used as an intermediate in the preparation of pseudonorephedrine oxazolidinone derivatives. These derivatives are valuable in the synthesis of various pharmaceutical compounds, particularly those with potential therapeutic applications.
Used in Organic Chemistry:
As a chiral building block, (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone is utilized in organic chemistry for the synthesis of enantiomerically pure compounds. Its unique stereochemistry allows for the creation of complex molecules with specific biological activities, making it a valuable tool in the development of new drugs and other chemical products.

Upstream product

• 2492-30-0 acetophenone semicarbazone 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 104863-92-5 (1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol 
• 113322-99-9 tert-butyl ((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)carbamate 
• 57-13-6 urea 
• 873-66-5 1-propenylbenzene 
• 51-79-6 urethane 
• 492-41-1 (1R,2S)-norephedrine 
• 54064-02-7 benzyl [(1S)-1-methyl-2-oxo-2-phenylethyl]carbamate 
• 591-51-5 phenyllithium 
• 58550-13-3 (1S,2S)-(+)-norpseudoephedrine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 36482-33-4 (2RS,3SR)-3-hydroxy-2-methyl-3-phenyl-propionic acid hydrazide 
• 48115-38-4 norepinephrine 

Downstream Products

• 90-82-4 pseudoephedrine 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 146402-89-3 (4S,5S)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)-acetyl]-oxazolidin-2-one 
• 1035485-35-8 C₂₂H₁₈ClNO₃ 
• 1035485-34-7 (4S,5S)-3-(4-(4-chlorophenoxy)phenyl)-5-methyl-4-phenyloxazolidin-2-one 
• 54680-46-5 norephedrine 
• 42746-64-5 4r-methyl-3-nitroso-5t-phenyl-oxazolidin-2-one 
• 4830-43-7 (1RS,2RS)-2-isopropylamino-1-phenyl-propan-1-ol 
• 130258-52-5 (4S,5R)-3-<(R)-5,6-(Isopropylidenedioxy)hexanoyl>-4-methyl-5-phenyl-1,3-oxazolidin-2-one 
• 142956-08-9 (4S,5R)-3-(3,3-Diphenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 147900-34-3 (4S,5R)-3-(2-5H-Dibenzo[a,d]cyclohepten-5-yl-acetyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 157555-77-6 (4S,5R)-3-<(S)-2,2-dimethyl-1,3-dioxolane-4-propanoyl>-4-methyl-5-phenyl-2-oxazolidinone 
• 164913-51-3 (4S,5R)-4-methyl-3-<(2R,3S)-2-methyl-3-phenyl-3-(tosylamino)propionyl>-5-phenyloxazolidin-2-one 
• 174590-89-7 (4S,5R)-3-(5-bromovaleryl)-4-methyl-5-phenyl-2-oxazolidinone 

Relevant articles and documents

Stereoselective synthesis of oxazolidin-2-ones via an asymmetric aldol/curtius reaction: Concise total synthesis of (?)-cytoxazone

Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (?)-cytoxazone. Consisting of three steps, this is one of the shortest syntheses reported to date. Ultimately, this convenient platform would provide a promising method for the early phases of drug discovery.

Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines

α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.

A new type of L-Tertiary leucine-derived ligand: Synthesis and application in Cu(II)-catalyzed asymmetric Henry reactions

A new series of Schiff bases derived from amino acids were developed as chiral ligands for Cu(II)-catalyzed asymmetric Henry reactions. The optimum ligand 7d exhibited outstanding catalytic efficiency in the Cu(II)-catalyzed asymmetric Henry additions of four nitroalkanes to different kinds of aldehydes to produce 76 desired adducts in high yields (up to 96%) with excellent enantioselectivities, up to 99% enantiomeric excess (ee).

Tandem copper and photoredox catalysis in photocatalytic alkene difunctionalization reactions

Oxidative alkene difunctionalization reactions are important in synthetic organic chemistry because they can install polar functional groups onto simple non-polar alkene moieties. Many of the most common methods for these reactions rely upon the reactivity of pre-oxidized electrophilic heteroatom donors that can often be unstable, explosive, or difficult to handle. Herein, we describe a method for alkene oxyamination and diamination that utilizes simple carbamate and urea groups as nucleophilic heteroatom donors. This method uses a tandem copper–photoredox catalyst system that is operationally convenient. The identity of the terminal oxidant is critical in these studies. Ag(I) salts proved to be unique in their ability to turn over the copper cocatalyst without deleteriously impacting the reactivity of the organoradical intermediates.

FACTOR XIIa INHIBITORS

The present invention provides a compound of Formula (I) and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIIa inhibitors.

Chiral 1,3,2-Diazaphospholenes as Catalytic Molecular Hydrides for Enantioselective Conjugate Reductions

Secondary 1,3,2-diazaphospholenes have a polarized P?H bond and are emerging as molecular hydrides. Herein, a class of chiral, conformationally restricted methoxy-1,3,2-diazaphospholene catalysts is reported. We demonstrate their catalytic potential in asymmetric 1,4-reductions of α,β-unsaturated carbonyl derivatives, including enones, acyl pyrroles, and amides, which proceeded in enantioselectivities of up to 95.5:4.5 e.r.

Kinetic resolution of racemic amino alcohols through intermolecular acetalization catalyzed by a chiral Bronsted acid

The kinetic resolution of racemic secondary alcohols is a fundamental method for obtaining enantiomerically enriched alcohols. Compared to esterification, which is a well-established method for this purpose, kinetic resolution through enantioselective intermolecular acetalization has not been reported to date despite the fact that the formation of acetals is widely adopted to protect hydroxy groups. By taking advantage of the thermodynamics of acetalization by the addition of alcohols to enol ethers, a highly efficient kinetic resolution of racemic amino alcohols was achieved for the first time and in a practical manner using a chiral phosphoric acid catalyst.

Oxazolidin-2-one-Pyrimidine Derivatives

The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

Open tubular molecular imprinted polymer fabricated in silica capillary for the chiral recognition of neutral enantiomers in capillary electrochromatography

In this study, we have expanded the applicability of the pre-established generalized preparation protocol to MIPs with a neutral template. The (4S,5R)-4-methyl-5-phenyl-2-oxazolidinone MIP layer was formed inside a pretreated and silanized fused silica capillary, and its chiral separation performance was examined. Optimization of chiral separation was also carried out. This is the very first report of somewhat successful application of the generalized preparation protocol to a MIP with a genuine neutral template. Copyright