66866-65-7

Basic information

• Product Name: 3-Oxazolidinecarboxylic acid, 4-[(1S)-1-methylpropyl]-5-oxo-, phenylmethyl ester, (4S)-
• CAS NO: 66866-65-7
• Molecular Formula: C15H19NO4
• Molecular Weight: 277.31600
• Mol File: 66866-65-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-Oxazolidinecarboxylic acid, 4-[(1S)-1-methylpropyl]-5-oxo-, phenylmethyl ester, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxazolidinecarboxylic acid, 4-[(1S)-1-methylpropyl]-5-oxo-, phenylmethyl ester, (4S)-(66866-65-7)
• EPA Substance Registry System: 3-Oxazolidinecarboxylic acid, 4-[(1S)-1-methylpropyl]-5-oxo-, phenylmethyl ester, (4S)-(66866-65-7)

Safety Data

• Hazardous Substances Data: 66866-65-7(Hazardous Substances Data)

Upstream product

• 73-32-5 L-isoleucine 
• 501-53-1 benzyl chloroformate 
• 319-78-8 isoleucine 
• 3160-59-6 N-benzyloxycarbonyl-isoleucine 
• 50-00-0 formaldehyd 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 61548-98-9 C₉H₉NO₂C₂H₃CHC 

Downstream Products

• 922705-52-0 (3R,4S)-4-methyl-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid 
• 922705-71-3 phenylmethyl [(1S,2S)-1-(diazoacetyl)-2-methylbutyl]methylcarbamate 
• 4125-95-5 (S)-Z-N-Methylisoleucine 
• 163887-30-7 N-Z-N-Me-(S,R)-Ile 
• 42417-66-3 (2S,3S)-3-methyl-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid 
• 6216-62-2 (2S,3S)-2-<(benzyloxycarbonyl)amino>-3-methylpentan-1-ol 

Relevant articles and documents

A novel synthesis of N-but-3-enyl-α- and β-amino acids

N-But-3-enyl-α- and β-amino acids can be prepared by cleaving 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones in the presence of allylsilanes and boron trifluoride etherate at room temperature in good to excellent yields. Georg Thieme Verlag Stuttgart.

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.

SYNTHESIS OF DERIVATIVES OF OXAZOLIDIN-5-ONES

A method has been developed for the synthesis of derivatives of oxazolidin-5-one by the reaction of the corresponding N-benzyloxycarbonylaminoacid with formaldehyde in the presence of formic acid.Yields of derivatives of 3-benzyloxycarbonyloxazolidin-5-on