104057-71-8

Basic information

• Product Name: (2S,4R)-3-benzoyl-4-benzyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one
• Synonyms: (2S,4R)-3-benzoyl-4-benzyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one
• CAS NO: 104057-71-8
• Molecular Weight: 351.445
• Mol File: 104057-71-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,4R)-3-benzoyl-4-benzyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-3-benzoyl-4-benzyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one(104057-71-8)
• EPA Substance Registry System: (2S,4R)-3-benzoyl-4-benzyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one(104057-71-8)

Safety Data

• Hazardous Substances Data: 104057-71-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 104057-64-9 (2S,4S)-3-benzoyl-2-(tert-butyl)-4-methyl-1,3-oxazolidin-5-one 
• 98-88-4 benzoyl chloride 

Downstream Products

• 17350-84-4 (R)-2-amino-2-methyl-3-phenylpropanoic acid 

Relevant articles and documents

N,O-Acetals from Pivalaldehyde and Amino Acids for the α-Alkylation with Self-Reproduction of the Center of Chirality. Enolates of 3-Benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones

The sodium salt of (S)-alanine, (S)-phenylalanine, (S)-valine, and (S)-methionine are condensed with pivalaldehyde to imines 5.Cyclization by treatment with benzoyl chloride in cold CH2Cl2 gives mainly (4:1 to > 99:1) the (2S,4S)-4-alkyl-3-benzoyl-2-(tert-butyl)-1,3-oxazolidin-5-ones (6; cis-configuration) in high yields (85-95 percent).The oxazolidinones 6 and 7 are deprotonated with lithium diethylamide (LDEA) in tetrahydrofuran (THF) and alkylated (MeI, benzyl bromide) or hydroxyalkylated (benzaldehyde) to 4,4-disubstituted oxazolidinones 9 and 10, respectively, with high diastereoselectivity (9:1 to 50:1; relative topicity ul).Hydrolysis of three of the oxazolidinones to amino acids of known configuration and optical purity indicates that little if any racemization occurs in the process.