97443-93-1

Basic information

• Product Name: (2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on
• Synonyms: (2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on
• CAS NO: 97443-93-1
• Molecular Weight: 302.417
• Mol File: 97443-93-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on(97443-93-1)
• EPA Substance Registry System: (2R,5S)-1-Benzoyl-2-(tert-butyl)-5-isopropyl-3-methylimidazolidin-4-on(97443-93-1)

Safety Data

• Hazardous Substances Data: 97443-93-1(Hazardous Substances Data)

Upstream product

• 630-19-3 pivalaldehyde 
• 87105-26-8 L-valine N-methylamide 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 98262-58-9 (2R,5S)-1-benzoyl-2-(tert-butyl)-5-isopropyl-3,5-dimethylimidazolidin-4-one 
• 4378-19-2 (S)-α-Methylvaline 

Relevant articles and documents

Herstellung enantiomerenreiner cis- oder trans-konfigurierter 2-(tert-Butyl)-3-methylimidazolidin-4-one aus den Aminosaeuren (S)-Alanin, (S)-Phenylalanin, (R)-Phenylglycin, (S)-Methionin und (S)-Valin.

In contrast to α-hydroxy and α-mercapto carboxylic acids, simple α-amino acids do not form acetal-type derivatives (2, X=NH) with pivalaldehyde.For the generation of amino-acid-derived chiral, nonracemic enolates (cf.3), and hence, for the α-alkylation of amino acids without racemization and without an external chiral auxiliary, the imidazolidinones 12-14 were prepared diastereoselectively.To this end, the methyl or ethyl esters of amino-acid hydrochlorides were first converted to N-methylamides of amino acids which in turn were condensed with pivalaldehyde to give (neopentylidenamino)amides (11).These Schiff bases could be cyclized either to trans- or to cis-imidazolidinones (12, 14 and 13, respectively), which were obtained in enantiomerically pure form after recrystallization.The enantiomeric purities were confirmed by HPLC with chiral stationary phases or by 1H-NMR spectroscopy in the presence of chiral shift reagents.The configurations (cis, trans) were assigned by NOE measurements on 300- or 360-MHz 1H-NMR spectrometers.