98262-63-6

Basic information

• Product Name: (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one
• Synonyms: (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one
• CAS NO: 98262-63-6
• Molecular Weight: 348.51
• Mol File: 98262-63-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one(98262-63-6)
• EPA Substance Registry System: (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one(98262-63-6)

Safety Data

• Hazardous Substances Data: 98262-63-6(Hazardous Substances Data)

Upstream product

• 97443-89-5 (2S,5S)-1-benzoyl-2-(tert-butyl)-3-methyl-5-(3'-thiabutyl)imidazolidin-4-one 
• 74-88-4 methyl iodide 

Downstream Products

• 109918-57-2 (2S,5R)-1-Benzoyl-2-(tert-butyl)-3,5-dimethyl-5-vinylimidazolidin-4-on 
• 109958-86-3 (R)-2-amino-2-methyl-3-butenoic acid 
• 109918-65-2 (R)-2-methylhomoserine 
• 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

α-Alkylation of Amino Acids without Racemization. Preparation of Either (S)- or (R)-α-Methyldopa from (S)-Alanine

Enantiomerically pure cis- and trans-5-alkyl-1-benzoyl-2-(tert-butyl)-3-methylimidazolidin-4-ones (1, 2, 11, 15, 16) and trans-2-(tert-butyl)-3-methyl-5-phenylimidazolidin-4-one (20), readily available from (S)-alanine, (S)-valine, (S)-methionine, and (R)-phenylglycine are deprotonated to chiral enolates (cf. 3, 4, 12, 21).Diastereoselective alkylation of these enolates to 5,5-dialkyl- or 5-alkyl-5-arylimidazolidinones (5, 6, 9, 10, 13a-d, 17, 18, 22) and hydrolysis give α-alkyl-α-amino acids such as (R)- and (S)-α-methyldopa (7 and 8a, resp.), (S)-α-methylvaline (14), and (R)-α-methyl-methionine (19).The configuration of the products is proved by chemical correlation and by NOE 1H-NMR measurements (see 23, 24).In the overall process, a simple, enantiomerically pure α-amino acid can be α-alkylated with retention or with inversion of configuration through pivalaldehyde acetal derivatives.Since no chiral auxiliary is required, the process is coined 'self-reproduction of a center of chirality'.The method is compared with other α-alkylations of amino acids occuring without racemization.The importance of enantiomerically pure, α-branched α-amino acids as synthetic intermediates and for the preparation of biologically active compounds is discussed.