2020/03/25 by Pradeep S. Chauhan, Skye Brettell, Ramakotaiah Mulamreddy +8
Biochemistry, Genetics and Molecular Biology · Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Carbohydrate Chemistry and Synthesis #Chemical Synthesis and Analysis #Fluorine in Organic Chemistry
paper · doi:10.1139/cjc-2020-0052
openalex publication_date 2020/03/25 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28
N′-Alkyl hydrazides were effectively synthesized by routes featuring installation, alkylation, and removal of a trifluoroacetyl group. A set of amino acid derived hydrazides were acylated using trifluoroacetic anhydride, and the resulting trifluoroacetyl hydrazides were alkylated with alcohols in Mitsunobu reactions and with alkyl halides under alkaline conditions. Removal of the trifluoroacetyl group was affected under reductive and hydrolytic conditions to provide the respective N′-alkyl hydrazides. This three-step process may be performed without isolation of intermediates to yield N′-alkyl hydrazide after a single chromatographic purification.