196214-76-3

Upstream product

• 3479-47-8 Z-Asp(OBzl)-OH 
• 23632-66-8 (4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one 
• 1152-61-0 N-Cbz-L-Asp 
• 207731-06-4 phenylmethyl (4S)-5-oxo-4-{2-oxo-2-[(phenylmethyl)oxy]ethyl}-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 922705-85-9 phenylmethyl (3S)-5-diazo-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)-4-oxopentanoate 
• 1445443-43-5 (S)-benzyl 3-(benzyloxycarbonylamino)-4-hydroxybutanoate 
• 1445443-71-9 C₂₀H₂₁NO₅ 
• 1445444-03-0 (3R)-N-benzyloxycarbonyl-3-aminomethyl-2-hydroxy-1-nitro-4-benzyloxycarbonylhexane 
• 1445444-38-1 (3R)-N-benzyloxycarbonyl-3-aminomethyl-1-nitro-4-benzyloxycarbonylhexane 
• 922705-87-1 (3R)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)-5-oxo-5-[(phenylmethyl)oxy]pentanoic acid 

Relevant academic research and scientific papers

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.

The facile production of N-methyl amino acids via oxazolidinones

A range of oxazolidinones derived from N-carbamoyl α-amino acids were prepared by an efficient method as key intermediates in the synthesis of N-methyl amino acids and peptides. The method was readily applied to most α-amino acids except those with basic side chains. The oxazolidinones were converted by reductive cleavage into N-methyl α-amino acids. CSIRO 2000.