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The Synthesis of N(S)-Alkoxyethyl-Substituted Aminonaphthalenesulfonamides by Opening of an Aziridene Ring
08 March 2002 (online)
N(S)-Alkoxyethyl-substituted 5-aminonaphthalenesulfonamides 4 (ANSA) can be obtained by a sulfonylaziridine ring opening. 5-Nitro(or 5-benzyloxycarbonylamino)-1-naphthalenesulfonyl chloride (1) reacts with aziridine in triethylamine/methanol to give stable 5-substituted naphthalene-sulfonylaziridines 2 (NSAz) in high yields. The subsequent opening of the aziridine ring is achieved by short-term heating of 2 in an alcohol in the presence of a catalytic amount of acetic acid-boron trifluoride complex to give 3 in nearly quantitative yields. After deprotection [hydrogen bromide/acetic acid or hydrogen/-palladium for benzyloxyoxycarbonyl (Cbz), or hydrogen/palladium for nitro] ANSAs were obtained. ANSAs are used as the detectable group in fluorescent peptide substrates for protease determination.