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- W2004398076 abstract "Selective Amide Cleavage in Peptides Containing α,α-Disubstituted α-Amino Acids A new synthesis of dipeptides with terminal α,α-disubstituted α-amino acids, using 2,2-disubtituted 3-amino-2H-azirines 1 as amino-acid equivalents, is demonstrated. The reaction of 1 with N-protected amino acids leads to the corresponding dipeptide amides in excellent yield. It is shown that the previously described selective hydrolysis (HCl, toluene, 80°, or HCl, MeCN/H2O, 80°) of the terminal amide group results in an extensive epimerization of the second last amino acid. An acid-catalyzed enolization in the intermediate oxazole-5(4H)-ones is responsible for this loss of configurational integrity. In the present paper, a selective hydrolysis of the terminal amide group under very mild conditions is described: In 3N HCl (THF/H2O 1:1), the dipeptide N,N-dimethylamides or N-methytlanilides are hydrolized at 25–35° to the optically pure dipeptides in very good yield." @default.
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- W2004398076 date "1987-03-18" @default.
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- W2004398076 title "Selektive Amidspaltung bei Peptiden mit ?,?-disubstituierten ?-Aminos�uren" @default.
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- W2004398076 doi "https://doi.org/10.1002/hlca.19870700213" @default.
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