114715-76-3

Upstream product

• 186581-53-3 diazomethane 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 41446-04-2 Z-Ile-O-COOiBu 

Downstream Products

• 59109-39-6 (3-bromo-1-(S)-(1-methylpropyl)-2-oxopropyl)carbamic acid benzyl ester 
• 152359-74-5 [(1S,2S)-1-(2,2-Dihydroxy-acetyl)-2-methyl-butyl]-carbamic acid benzyl ester 
• 268747-19-9 [(1S,2S)-2-Methyl-1-(2-oxo-acetyl)-butyl]-carbamic acid benzyl ester 
• 1027083-91-5 [(1S,2S)-1-(5,6-Dihydro-pyrazin-2-yl)-2-methyl-butyl]-carbamic acid benzyl ester 
• 147224-29-1 [(1S,2S)-1-(2-Azido-acetyl)-2-methyl-butyl]-carbamic acid benzyl ester 
• 269085-43-0 2-phenyl-4-(1-(S)-benzyloxycarbonylamino-2-methylbutyl)-1H-imidazole 
• 852248-41-0 2-phenyl-4-(1-(S)-amino-2-methylbutyl)-1H-imidazole 
• 922705-52-0 (3R,4S)-4-methyl-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)hexanoic 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.

Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids

A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available

Enantiopure N-protected α-amino glyoxals 1. Synthesis from α-amino acids and some condensation reactions with amines

A series of N-protected α-ammo diazoketones has been prepared from L-amino acids and dipeptides and used as precursors in the synthesis of novel N-protected α-amino glyoxals via oxidation with distilled dimethyldioxirane (DMD) in acetone. The glyoxals have been converted, without purification, into enantiopure imines, pyrazines, quinoxalines, and pyrido[2,3-b]pyrazines via condensation with the appropriate amine or diamine. The molecular structure of the pyrido[2,3-b]pyrazine derived from N-Cbz-L-phenylalanine has been determined by X-ray analysis.

SYNTHESIS OF DIAZOKETONES DERIVED FROM α-AMINO ACIDS; PROBLEM OF SIDE REACTIONS

Optimum conditions of synthesis of eight diazoketones derived from optically active N-(t-butyloxycarbonyl)- and N-benzyloxycarbonylamino acids have been described.The problem of formation of by-products during Arndt-Eistert synthesis of β-homoamino acids at the stage of reaction of mixed anhydride with a weak nucleophile-diazomethane - has been discussed.