213887-92-4

Basic information

• Product Name: (S)-4-(1-methylethyl)-3-<(R)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one
• Synonyms: (S)-4-(1-methylethyl)-3-<(R)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one
• CAS NO: 213887-92-4
• Molecular Weight: 427.543
• Mol File: 213887-92-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-4-(1-methylethyl)-3-<(R)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(1-methylethyl)-3-<(R)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one(213887-92-4)
• EPA Substance Registry System: (S)-4-(1-methylethyl)-3-<(R)-2-methyl-1-oxo-3-phenylpropyl>-5,5-diphenyloxazolidin-2-one(213887-92-4)

Safety Data

• Hazardous Substances Data: 213887-92-4(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 213887-84-4 (S)-4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyloxazolidin-2-one 
• 213887-81-1 (S)-5,5-Diphenyl-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one 
• 74-88-4 methyl iodide 
• 184346-45-0 (S)-5,5-Diphenyl-4-isopropyl-1,3-oxazolidin-2-one 
• 72-18-4 L-valine 
• 108-86-1 bromobenzene 
• 6306-52-1 L-valine methylester hydrochloride 
• 100-58-3 phenylmagnesium bromide 
• 4070-48-8 L-Valine methyl ester 
• 78603-95-9 1,1-diphenyl-L-valinol 

Downstream Products

• 218800-56-7 (S)-3-((R)-2-<<(benzyloxycarbonyl)amino>methyl>-1-oxo-3-phenylpropyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 218800-60-3 (S)-3-<(R)-3-hydroxy-1-oxo-2-(phthalimidomethyl)propyl>-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 218800-54-5 (S)-3-((R)-2-<<(benzyloxycarbonyl)amino>methyl>-3-methyl-1-oxobutyl)-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 218800-39-6 (S)-3-<3-<4-(benzyloxy)phenyl>-1-oxopropyl>-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 218800-38-5 (S)-4-(1-methylethyl)-3-<1-oxo-3-phthalimidopropyl>-5,5-diphenyloxazolidin-2-one 

Relevant articles and documents

Highly effective and recyclable chiral auxiliaries: A study of the synthesis and use of three 4-isopropyl-5,5-diaryloxazolidin-2-ones

A series of three 5,5-diaryl substituted oxazolidin-2-ones (diphenyl, dinaphthyl and ditolyl) have been synthesised. Studies on the benzylation of the lithium enolates of N-acyl derivatives reveal that the yields obtained were sensitive to the method of quenching the reaction. This was particularly acute for the 5,5-diphenyl system where effective yields (69%) and high diastereoselectivities (dr 98 : 2) are only observed when the reactions were quenched into aqueous buffer. Methylation studies on the N-acyl derivatives showed that the most advantageous results (58-69%, dr ≥ 91 : 9) were only observed using the sodium enolates. The 5,5-ditolyl-4-isopropyloxazolidin-2-one proved to be more efficacious in terms of efficiency and diastereoselectivity (dr ≥ 97 : 3). Subsequent, simple alkaline hydrolyses of the alkylation products allowed for the high recovery and recyclability of the 5,5-diaryl substituted oxazolidin-2-ones without any deleterious endocyclic cleavage. In addition, the acyl portions were recovered in high yield from the alkaline hydrolyses without any evidence of racemisation.

A study of 4-substituted 5,5-diaryl oxazolidin-2-ones as efficacious chiral auxiliaries

A series of three 5,5-diaryl substituted oxazolidin-2-ones (diphenyl, dinaphthyl and ditolyl) have been prepared and shown to be particularly effective chiral auxiliaries to afford high yields and diastereoselectivities for alkylation and azidations of their N-acyl derivatives. The 5,5-ditolyl oxazolidin-2-one proved to be particularly efficacious in terms of diastereoselectivity, yield and solubility.