97443-89-5

Basic information

• Product Name: (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one
• Synonyms: (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one
• CAS NO: 97443-89-5
• Molecular Weight: 334.483
• Mol File: 97443-89-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one(97443-89-5)
• EPA Substance Registry System: (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one(97443-89-5)

Safety Data

• Hazardous Substances Data: 97443-89-5(Hazardous Substances Data)

Upstream product

• 93-97-0 benzoic acid anhydride 
• 98-88-4 benzoyl chloride 
• 630-19-3 pivalaldehyde 
• 68800-02-2 (S)-2-amino-N-methyl-4-(methylthio)butanamide 

Downstream Products

• 98262-63-6 (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one 
• 109918-58-3 (2S,5R)-1-Benzoyl-2-(tert-butyl)-5-ethyl-3-methyl-5-vinylimidazolidin-4-on 
• 109918-57-2 (2S,5R)-1-Benzoyl-2-(tert-butyl)-3,5-dimethyl-5-vinylimidazolidin-4-on 
• 101055-56-5 (2S)-1-benzoyl-2-(1,1-dimethylethyl)-3-methyl-4-imidazolidinone 
• 98302-79-5 D-α-methylmethionine 

Relevant articles and documents

Process for the enantioselective production of α-vinyl-α-aminocarboxylic acids

α-Vinyl-α-aminocarboxylic acids of the general formula: STR1 where * indicates a center of asymmetry and R is hydrogen, deuterium, lower alkyl, allyl, benzyl, or benzyl substituted 1 to 3 times by alkyl, alkoxy, fluorine or chlorine and produced enantiose

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.