213887-83-3

Basic information

• Product Name: (S)-5,5-Di(4'-tolyl)-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one
• Synonyms: (S)-5,5-Di(4'-tolyl)-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one
• CAS NO: 213887-83-3
• Molecular Weight: 441.57
• Mol File: 213887-83-3.mol

Chemical Properties

• CAS DataBase Reference: (S)-5,5-Di(4'-tolyl)-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5,5-Di(4'-tolyl)-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one(213887-83-3)
• EPA Substance Registry System: (S)-5,5-Di(4'-tolyl)-4-isopropyl-3-(1'-oxo-3'-phenylpropyl)-1,3-oxazolidin-2-one(213887-83-3)

Safety Data

• Hazardous Substances Data: 213887-83-3(Hazardous Substances Data)

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 213887-79-7 (S)-5,5-Di(4'-tolyl)-4-isopropyl-1,3-oxazolidin-2-one 
• 72-18-4 L-valine 
• 106-38-7 para-bromotoluene 
• 6306-52-1 L-valine methylester hydrochloride 
• 213887-77-5 (S)-2-Amino-1,1-di(4'-tolyl)-3-methylbutan-1-ol 
• 4294-57-9 para-methylphenylmagnesium bromide 

Downstream Products

• 366446-27-7 (2''S,4S)-5,5-Di(4'-tolyl)-3-(2''-bromo-3''-phenyl-1''-oxopropyl)-4-isopropyl-1,3-oxazolidin-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.