2-(Hexyloxy)ethyl 4-methylbenzenesulfonate → 3-(((benzyloxy)carbonyl)amino)-N-(2-(hexyloxy)ethyl)-N,N,3-trimethylbutan-1-aminium 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl(4-(dimethylamino)-2-methylbutan-2-yl)carbamate (0.72 g, 2.7 mmol) and 2-(hexyloxy)ethyl 4-methylbenzenesulfonate (1.8 g, 6.0 mmol) was stirred overnight at 75° C. The crude reaction mixture was purified by reverse phase HPLC eluting from a C18 column with a gradient of 5 to 95% CH3CN in water (with 0.01% acetic acid) to give 0.96 g of white solid (64% yield). 1H NMR (400 MHz, D2O) δ 0.75-78 (m, 3H), 1.18 (s, 6H), 1.44-1.27 (m, 2H), 2.06 (br m, 2H), 2.29 (s, 3H), 3.03 (s, 6H), 3.17-3.21 (m, 2H), 3.30 (br m, 2H), 3.36-3.39 (t, J=6.5 Hz, 2H), 3.67 (br s, 2H), 4.97 (br s, 2H), 7.26-7.28 (d, J=8.1 Hz, 2H), 7.30-7.37 (m, 5H), 7.58-7.60 (d, J=8.1 Hz, 2H). LRMS (ESI/APCI) m/z 393 [M]+.

Provenance & Evidence