119906-44-4

Basic information

• Product Name: (2S,5R)-5-(O-benzoyl-1-methyl-1-hydroxyethyl)-2-t-butyl-3-methyl-4-imidazolidinone
• CAS NO: 119906-44-4
• Molecular Weight: 318.416
• Mol File: 119906-44-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,5R)-5-(O-benzoyl-1-methyl-1-hydroxyethyl)-2-t-butyl-3-methyl-4-imidazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-5-(O-benzoyl-1-methyl-1-hydroxyethyl)-2-t-butyl-3-methyl-4-imidazolidinone(119906-44-4)
• EPA Substance Registry System: (2S,5R)-5-(O-benzoyl-1-methyl-1-hydroxyethyl)-2-t-butyl-3-methyl-4-imidazolidinone(119906-44-4)

Safety Data

• Hazardous Substances Data: 119906-44-4(Hazardous Substances Data)

Upstream product

• 119838-36-7 (R)-2-tert-butyl-3-methyl-4-oxoimidazolidinium (R)-mandelate 
• 17199-29-0 (S)-Mandelic acid 
• 101055-57-6 (2R)-1-benzoyl-2-(1,1-dimethylethyl)-3-methyl-4-imidazolidinone 
• 67-64-1 acetone 
• 101055-55-4 (+/-)-2-(tert-butyl)-3-methylimidazolidin-4-one 

Downstream Products

• 2280-48-0 (R)-(-)-β-hydroxyvaline 

Relevant articles and documents

RESOLUTION AND USE IN α-AMINO ACID SYNTHESIS OF IMIDAZOLIDINONE GLYCINE DERIVATIVES

The imidazolidinones (rac.-1 and rac.-2) obtained from pivalaldehyde and glycine amides are resolved efficiently by crystallization of diastereomeric ammonium salts with chiral acids (mandelates and a gulonate respectively).The free bases are acylated under Schotten-Baumann conditions to give enantiomerically pure 1-Bz-, 1-BOC-, 1-Z- or 1-formyl-2-t-butyl-3-methyl- or -3-benzyl-4-imidazolidinones.Diastereoselective alkylation of the 3-methyl derivatives (BMI) with a variety of electrophiles (LDA/THF -70 to +25 degC) gives trans-disubstituted imidazolidinones exclusively (3-22).Some of these are hydrolyzed by a procedure employing excess acidic ion exchange resin to give enantiomerically pure (R)- or (S)-amino acids.The procedure is compared with other methods of generating chiral glycine enolates.