Activation of carboxylic acids by pyrocarbonates. Synthesis of arylamides of N-protected amino acids and small peptides using dialkyl pyrocarbonates as condensing reagents.
Activation of carboxylic acids was achieved via dialkyl pyrocarbonates (ROCO)2O, (R = ethyl, isopropyl, sec-butyl, tert-butyl) in aprotic solvents in the presence of tertiary amines. A convenient one-pot procedure for the preparation of arylamides from N-protected amino acids including arginine and from di-tert-butyl pyrocarbonate in the presence of pyridine (Boc2O-pyridine system) was reported. Analogously, diisopropyl, di-sec-butyl or diethyl pyrocarbonate could be used in the presence of N-methylmorpholine or triethylamine. A wide variety of N-protected amino acid arylamides were prepared in good yields.
Pozdnev
V F
VF
Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, Moscow.
D000577:Amides / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D004047:Diethyl Pyrocarbonate / Q000031:analogs & derivatives* / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry
D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D010455:Peptides; D011725:Pyridines; C079227:pyrocarbonic acid; D004047:Diethyl Pyrocarbonate; C023666:pyridine