311310-18-6

Basic information

• Product Name: 2-Oxazolidinone, 4-(1-methylethyl)-3-[(2R)-1-oxo-2-phenylpropyl]-, (4S)-
• CAS NO: 311310-18-6
• Molecular Formula: C15H19NO3
• Molecular Weight: 261.321
• Mol File: 311310-18-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 4-(1-methylethyl)-3-[(2R)-1-oxo-2-phenylpropyl]-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 4-(1-methylethyl)-3-[(2R)-1-oxo-2-phenylpropyl]-, (4S)-(311310-18-6)
• EPA Substance Registry System: 2-Oxazolidinone, 4-(1-methylethyl)-3-[(2R)-1-oxo-2-phenylpropyl]-, (4S)-(311310-18-6)

Safety Data

• Hazardous Substances Data: 311310-18-6(Hazardous Substances Data)

Upstream product

• 25145-43-1 2-phenylpropionyl chloride 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 219951-25-4 (+/-)-pentafluorophenyl 2-phenylpropionate 
• 264621-69-4 ethyl (S)-2-oxooxazolidinine-4-carboxylate 
• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 54705-41-8 (5R)-5-phenyl-1,3-oxazolidin-2-one 
• 492-37-5 hydratropic acid 
• 878194-06-0 (R)-pentafluorophenyl 2-phenylpropionate 
• 17016-83-0 4-isopropyloxazolidin-2-one 
• 103422-95-3 (S)-4-iso-propyl-3-(2'-phenylacetyl)oxazolidin-2-one 
• 74-88-4 methyl iodide 

Downstream Products

• 878194-06-0 (R)-pentafluorophenyl 2-phenylpropionate 
• 177697-55-1 (4S)-4-phenyl-3-[(2R)-2-phenylpropionyl]oxazolidin-2-one 
• 198344-48-8 (4R,2'R)-3-(2'-phenylpropionyl)-4-phenyl-oxazolidin-2-one 
• 311310-15-3 (4S,2'S)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one 
• 1308658-81-2 C₁₅H₁₈ClNO₃ 
• 7782-26-5 (R)-2-Phenylpropionic acid 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 

Relevant articles and documents

Efficient parallel resolution of pentafluorophenyl active esters using quasi-enantiomeric combinations of oxazolidin-2-ones

The parallel resolution of racemic pentafluorophenyl 2-aryl/ phenylpropanoates and butanoates using an equimolar combination of quasi-enantiomeric Evans oxazolidin-2-ones is discussed. The levels of diastereoselectivity were excellent (>90% de) leading to separable quasi-enantiomeric oxazolidin-2-ones in good yield. This methodology was used to resolve a series of structurally related 2-aryl/phenylpropanoic and butanoic acids.

Resolution of pentafluorophenyl 2-phenylpropanoate using combinations of quasi-enantiomeric oxazolidin-2-ones

The kinetic, mutual and parallel resolution of a series of structurally related active esters derived from 2-phenylpropanoic acid using a combination of quasi-enantiomeric oxazolidin-2-ones is discussed.

Resolution of pentafluorophenyl esters using oxazolidin-2-ones

A series of structurally related racemic pentafluorophenyl active esters were resolved using an equimolar amount of (S)-4-phenyloxazolidin-2-one. The levels of diastereocontrol were found to be excellent (80-96% de) at ～40% conversion.

Parallel kinetic resolution of racemic oxazolidinones using quasi-enantiomeric active esters

Racemic Evans' oxazolidinones were efficiently resolved using a combination of quasi-enantiomeric profens. The levels of stereocontrol were high, leading to products with predictable configurations.

SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels-Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions. The Royal Society of Chemistry 2006.

Investigations into the parallel kinetic resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric oxazolidinones

The resolution of 2-phenylpropanoyl chloride using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereoselectivity were found to be dependent upon the structural nature of the metallated oxazolidinone, temperature and metal counter-ion.

Efficient parallel resolution of an active ester of 2-phenylpropionic acid using quasi-enantiomeric Evans' oxazolidinones

The parallel kinetic resolution of pentafluorophenyl 2-phenylpropionate using an equimolar combination of quasi-enantiomeric oxazolidinones is discussed. The levels of diastereocontrol were excellent leading to separable quasi-enantiomeric syn-oxazolidino

Copper(II)-catalyzed kinetic resolution of (±)-2-arylpropionic acids with chiral N-trimethylsilyloxazolidin-2-one

The reaction between (±)-2-arylpropanoyl chlorides 1 (2 equiv.) and enantiopure N-trimethylsilyloxazolidin-2-one 2 in the presence of a catalytic amount of CuCl2 in hexane affords the corresponding N-acyloxazolidin-2-one in good chemical yields (97%) with up to 50% de.