Acylation of hydrazides with acetic acid and formic acid.
In peptide synthesis, hydrazides are important intermediates for the azide coupling method. A hydrazide is converted to the corresponding azide in the presence of an acid and a nitrite. When acetic acid (or formic acid) is used as the acid, partial acetylation (or formylation) of the hydrazide occurs as a side reaction. Formylation of the hydrazide is much faster than acetylation. Removal of the formyl group on the hydrazide with hydrazine and hydroxylamine was studied. The rate of deformylation with hydrazine treatment is faster than that with hydroxylamine treatment.
Hojo
Keiko
K
Faculty of Pharmaceutical Sciences and High Technology Research Center, Kobe Gakuin University, Japan.
Maeda
Mitsuko
M
Smith
Timothy J
TJ
Kawasaki
Koichi
K
D019342:Acetic Acid / Q000737:chemistry*; D000215:Acylation; D002851:Chromatography, High Pressure Liquid; D005561:Formates / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*
D005561:Formates; D006834:Hydrazines; C030544:formic acid; D019342:Acetic Acid