Trifluoroacetic acid → N-(5-aminopentyl)-N-methyl-2-nitrobenzenesulfonamide

Participants

Reaction Steps

A solution of tert-butyl 5-(N-methyl-2-nitrophenylsulfonamido)pentylcarbamate 30d (31.5 g, 79 mmoles) and trifluoro acetic acid (29.2 mL, 5 eq) in DCM (300 mL) was stirred at RT until completion (˜16 h). The RM was then concentrated under vacuo, redissolved in DCM, washed with a saturated sodium bicarbonate aqueous solution (2 times), then brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 23.7 g (quantitative yield) of N-(5-aminopentyl)-N-methyl-2-nitrobenzenesulfonamide 26a as a slightly yellow solid; m/z 302 [M+H]+.

Provenance & Evidence