266338-68-5

Upstream product

• 529-64-6 Tropic acid 
• 877610-02-1 3-hydroxy-N-[1-methyl-1-(N-methyl-N-phenylcarbamoyl)ethyl]-2-phenyl-propanamide 
• 266338-65-2 3-hydroxy-2-phenyl-N-[1-methyl-1-(N,N-dimethylcarbamoyl)ethyl]propanamide 

Downstream Products

• 304682-71-1 methyl-2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)ethanoate 
• 918159-31-6 rac-2-(2-hydroxy-1-phenylethyl)-4,4-dimethyl-1,3-oxazol-5(4H)-one 
• 304682-72-2 2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)ethanoic acid 
• 304682-74-4 2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-1-oxoethyl]amino}-2-methylpropanoic acid 
• 304682-73-3 2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-1-oxoethyl]amino}-2,N,N-trimethylpropanamide 
• 304682-76-6 2-[(2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-1-oxoethyl]amino}-2-methyl-1-oxopropyl)amino]ethanoic acid 
• 304682-75-5 methyl 2-[(2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-1-oxoethyl]amino}-2-methyl-1-oxopropyl)amino]ethanoate 
• 304682-56-2 2-({2-[(2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-1-oxoethyl]amino}-2-methyl-1-oxopropyl)amino]-1-oxoethyl}amino)-2,N,N-trimethylpropanamide 
• 266338-87-8 2-[(2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-2-methyl-1-oxopropyl]amino}-2-methyl-1-oxapropyl)amino]-2,N,N-trimethylpropanamide 
• 266338-79-8 2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-2-methyl-1-oxopropyl]amino}-2,N,N-trimethylpropanamide 
• 266338-83-4 2-{[2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-2-methyl-1-oxopropyl]amino}-2-methylpropanoic acid 
• 266338-75-4 2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methyl-1-oxopropyl}amino)-2-methylpropanoic acid 
• 266338-71-0 2-({2-[(3-hydroxy-1-oxo-2-phenylpropyl)amino]-2-methylpropyl}amino)-2,N,N-trimethylpropanamide 

Relevant academic research and scientific papers

cis-(6RS,13RS)-3,3,10,10-Tetramethyl-6,13-diphenyl-1,8-dioxa-4, 11-diazacyclotetradecane-2,5,9,12-tetraone and two of its precursors

The title macrocycle, C26H30N2O 6, (VI), was obtained by 'direct amide cyclization' from the linear precursor 3-hydroxy-N-[1-methyl-1-(N-methyl-N-phenylcarbamoyl)ethyl]-2- phenylpropanamide, the N-methylanilide

Synthesis of 16-membered cyclic depsipeptides via direct amide cyclization

The 2,2-disubstituted 2H-azirin-3-amines 5 (3-amino-2H-azirines) were used as synthons for α,α-disubstituted α-amino acids in the preparation of 16-membered cyclic depsipeptides 13. The linear precursors containing four α,α-disubstituted α-amino acids, the pentapeptides 12, were synthesized from β-hydroxy acids 4 via the 'azirine/oxazolone method' (Scheme 2). The 16-membered cyclic depsipeptides 13 were prepared via 'direct amide cyclization' in good-to-excellent yields (Schemes 3 and 4). In addition to the desired cyclic monomer 13, which was obtained as the main product, the cyclodimer 14 could also be isolated. The cyclization conditions were investigated and found to be optimum with HCl in toluene at 100°. The structure and conformation of the cyclic depsipeptide 13b was established by X-ray crystallography.