Acylation of Hydrazides with Acetic Acid and Formic Acid

• Published in: Chemical & pharmaceutical bulletin Vol. 50; no. 1; pp. 140 - 142
• Main Authors: Hojo, Keiko, Maeda, Mitsuko, Smith, Timothy J., Kawasaki, Koichi
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 2002; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: Acetic Acid - chemistry; acetylation; Acylation; acylation of hydrazide; Aliphatic compounds; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Chromatography, High Pressure Liquid; deformylation; Exact sciences and technology; Formates - chemistry; formylation; hydrazide; Hydrazines - chemistry; Life Sciences & Biomedicine; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; hydrazide; acetylation; formylation; acylation of hydrazide; deformylation; Organic hydrazide; α-Aminoacid; Formic acid; Acetylation; Kinetics; Formylation; Acetic acid; Acylation
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.50.140

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 hydroxyl-amine treatment.