143359-25-5

Basic information

• Product Name: (4S,5R)-(-)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone
• Synonyms: (4S,5R)-(-)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone
• CAS NO: 143359-25-5
• Molecular Weight: 266.727
• Mol File: 143359-25-5.mol

Chemical Properties

• CAS DataBase Reference: (4S,5R)-(-)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-(-)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone(143359-25-5)
• EPA Substance Registry System: (4S,5R)-(-)-(2'-chloroacetyl)-3,4-dimethyl-5-phenyl-2-imidazolidinone(143359-25-5)

Safety Data

• Hazardous Substances Data: 143359-25-5(Hazardous Substances Data)

Upstream product

• 112791-04-5 (4R,5S)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 79-04-9 chloroacetyl chloride 
• 92841-65-1 (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one 

Downstream Products

• 307304-63-8 (2R,4'R,5'S)-2-amino-3-(3,4-dimethoxyphenyl)-1-(3',5'-dimethyl-2'-oxo-4'-phenyl-1'-imidazolydinyl)propan-1-one 
• 307304-38-7 (4R,5S)-(+)-1-[2'-(diphenylmethyleneamino)acetyl]-3,4-dimethyl-5-phenyl-2-imidazolidinone 
• 307304-62-7 tert-butyl (4R,4'R,5'S)-4-amino-5-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-5-oxopentanoate 
• 307304-64-9 (3'R,4S,5R)-1,5-dimethyl-4-phenyl-3-(1',2',3',4'-tetrahydro-3'-isoquinolinylcarbonyl)-2-imidazolidinone 
• 307304-61-6 (2R,4'R,5'S)-2-amino-1-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-4-penten-1-one 
• 143396-13-8 (4S,5R)-1,5-Dimethyl-4-phenyl-3-(2-phenylsulfanyl-acetyl)-imidazolidin-2-one 
• 143359-27-7 (4R,5S)-1,5-Dimethyl-4-phenyl-3-((S)-3-phenyl-2-phenylsulfanyl-propionyl)-imidazolidin-2-one 
• 143359-41-5 (4S,5R)-1,5-Dimethyl-4-phenyl-3-((R)-3-phenyl-2-phenylsulfanyl-propionyl)-imidazolidin-2-one 
• 143359-29-9 (4S,5R)-1-((E)-(S)-5,9-Dimethyl-2-phenylsulfanyl-deca-4,8-dienoyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 143359-28-8 (4R,5S)-1,5-Dimethyl-3-((S)-5-methyl-2-phenylsulfanyl-hex-4-enoyl)-4-phenyl-imidazolidin-2-one 
• 307304-50-3 (2S,4'S,5'R)-2-amino-3-(1,3-benzodioxol-5-yl)-1-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)propan-1-one 

Relevant articles and documents

1,5-dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: Useful new reagents for practical asymmetric synthesis of α-amino acids

New 1,5-dimethyl-4-phenylimidazolidin-2-one-derived acyclic chiral iminic glycine reagents have been prepared and diastereoselectively alkylated with activated alkyl halides and electrophilic olefins in the presence of lithium chloride under (a) strong bases (LHMDS, KOBu(t)) and low temperature (-78 °C,) conditions; (b) solid-liquid phase-transfer catalysis reaction (LiOH, TBAB, -20 °C) conditions, and (c) in the presence of organic bases (DBU, BEMP, TMG, -20 °C). In the case of dielectrophiles C- and N-alkylation takes place to afford heterocyclic derivatives. Hydrolysis of alkylated products has been carried out (a) in two-step procedures with LiOOH or LiOH followed by acidic hydrolysis or Dowex purification, (b) in one single-step under refluxing water to give the corresponding α-amino acid, (c) in the presence of DBU in methanol to provide N-protected α-amino acids methyl esters, or (d) by a protection-hydrolysis procedure to afford N-Boc-protected α-amino acids. The chiral imidazolidinone has generally been recovered in good yield. This methodology has been shown to be useful for the synthesis of acyclic and heterocyclic (S)- and (R)-α-amino acids.

(4R,5S)-1,5-Dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative: Practical asymmetric synthesis of α-amino acids

The lithium enolate of enantiomerically pure N- [bis(methylthio)methylene] glycinate 11 derived from (4R,5S)-1,5-dimethyl-4- phenylimidazolidin-2-one reacts with alkyl halides giving the alkylated derivatives 12 with a high degree of control of the diastereoselectivity. These alkylated systems are easily hydrolyzed to the corresponding α-amino acids, the chiral auxiliary being recovered.

A new approach to 2-phenylthioalcohols in high optical purity

2-Phenylthioalcohols are prepared in high optical purity by alkylation of chiral imides of 2-phenylthioacetic acid, obtained starting from chiral imidazolidin-2-ones.