86217-47-2

Upstream product

• 2768-42-5 (R)-3-phenyl-3-hydroxypropionic acid 
• 15463-91-9 3-bromo-3-phenylpropionic acid 
• 5764-85-2 Ethyl 3-hydroxy-3-phenylpropanoate 
• 64-17-5 ethanol 
• 7803-57-8 hydrazine hydrate 
• 32803-73-9 methyl 3-phenyl-3-chloro-2-ketopropionate 
• 58692-70-9 methyl (R)-3-hydroxy-3-phenylpropanoate 

Downstream Products

• 103126-26-7 3-Hydroxy-3-phenylpropionyl azide 
• 621-82-9 Cinnamic acid 
• 302-01-2 hydrazine 
• 13047-12-6 5-phenylpyrazolidin-3-one 
• 86238-44-0 N-<(R)-1-(1-Naphthyl)ethyl>-(5S)-phenyl-2-oxazolidone-3-carboxamide 
• 86217-49-4 N-<(R)-1-(1-Naphthyl)ethyl>-(5R)-phenyl-2-oxazolidone-3-carboxamide 
• 7693-77-8 5-phenyloxazolidin-2-one 
• 4198-15-6 3-hydroxy-N,3-diphenylpropanamide 

Relevant academic research and scientific papers

Reactions of isomeric arylchloropyruvates and glycidates with hydrazines

Reactions of arylchloropyruvic acids esters with aryl- and hetarylhydrazines give rise to pyrazolinedione hydrazones as a result of a tandem condensation of the substituted hydrazines with arylchloropyruvates. In contrast to this process in reaction with hydrazine hydrate a ready reduction unexpectedly occurs by Kizhner-Wolff mechanism affording 3- hydroxydihydrocinnamic acid hydrazide as the principal product. The isomeric arylglycidate reacts along the same pattern. 2005 Pleiades Publishing, Inc.

Improved Chiral Derivatizing Agents for the Chromatographic Resolution of Racemic Primary Amines

Several 4- and/or 5-aryl-substituted 2-oxazolidones have been prepared and studied as chiral derivatizing agents (CDA) for the chromatographic resolution of chiral primary amines via diastereomeric allophanates.The diastereomeric allophanates derived from either racemic primary amines and cis-4,5-diphenyl-2-oxazolidone-3-carbamyl chloride or racemic isocyanates and cis-4,5-diphenyl-2-oxazolidone show sufficient NMR chemical shift differences and chromatographic separability that this heterocyclic system should prove to be a very useful CDA for the chromatographic resolution and determination of the absolute configuration of a variety of chiral primary amines.The diastereomeric allophanates are readily hydrolyzed to return both chiral components of the allophanates in excellent yield.Both solution and adsorbed conformations of these allophanates are discussed in reference to the determination of the absolute configuration of the allophanates (and hence of the chiral primary amine) from the senses of NMR nonequivalence between and chromatographic elution order of the diastereomers.