136436-80-1

Upstream product

• 136436-83-4 (4S)-3-<2'-(4-isobutylphenyl)ethanoyl>-4-(1-methylethyl)2-oxazolidinone 
• 74-88-4 methyl iodide 
• 71381-91-4 (+/-)-2-(4-isobutylphenyl)propanoyl chloride 
• 1553-60-2 ibufenac 
• 17016-83-0 4-isopropyloxazolidin-2-one 
• 851913-12-7 pentafluorophenyl (S)-2-(4-isobutylphenyl)propionate 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 313520-42-2 (+/-)-pentafluorophenyl 2-(4-isobutylphenyl)propionate 
• 264621-69-4 ethyl (S)-2-oxooxazolidinine-4-carboxylate 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 38588-43-1 p-isobutylphenylacetic acid chloride 

Downstream Products

• 51146-56-6 (S)-ibuprofen 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

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.

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.

On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one

The specific rotation of (S)-4-isopropyl-oxazolidin-2-one is extremely solvent dependent. In chloroform it is dextrorotatory {[α]D26 = + 15.5 (c 5.2, CHCl3)}, whereas in ethanol it is levorotatory {[α]D26 = - 16.1 (c 5.2, EtOH)}.

Asymmetric synthesis of 2-arylpropionic acids

The preparation of (S)-2-(6-methoxy-2-naphtyl)propionic acid (S-Naproxen) 1 and (S)-2-(4-isobutylphenyl)propionic acid (S-Ibuprofen) 2, based on asymmetric alkylation of oxazolidinones 9 and 14, is reported.