Benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate → 3-(((Benzyloxy)carbonyl)amino)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl 4-(dimethylamino)-2-methylbutan-2-ylcarbamate (0.54 g, 2 mmol) and [2-[2-(2-methoxyethoxy)ethoxy]ethoxy]p-toluenesulfonate (1.3 g, 4 mmol) was stirred overnight at 45° C. The crude reaction mixture was directly purified by reverse phase HPLC eluting from a C18 column with a gradient of 5 to 95% acetonitrile in water (with 0.01% acetic acid) to give a clear oil (0.95 g, 2.3 mmol). 1H NMR (D2O, 400 MHz) δ 1.18 (s, 6H), 2.05 (br m, 2H), 2.29 (s, 3H), 2.86 (s, 6H), 3.17-3.21 (m, 2H), 3.26 (s, 3H), 3.30 (br s, 2H), 3.48-3.56 (m, 8H), 3.71 (br s, 2H), 4.91 (br S, 2H), 7.25-7.27 (d, J=8.1 Hz, 2H), 7.30-7.36 (m, 5H), 7.57-7.59 (d, J=8.1 Hz, 2H); LRMS (ESI/APCI) m/z 411 [M]+

Provenance & Evidence