Diethyl Ether → 2,2'-(1,4,8,11-Tetraazacyclotetradecane-1,8-diyl)diacetic acid

Participants

Reaction Steps

To a solution of compound (4) (0.48 g, 0.96 mmol) in absolute ethanol (40 ml) was added 10% Pd/C (0.12 g). The resultant mixture was stirred at an ambient temperature under H2 atmosphere for 10 hours. The reaction mixture was filtered through a celite pad, and washed with ethanol (2×10 ml). The combined filtrate was evaporated in vacuo to give an oily residue, which was then treated with diethyl ether (Et2O) to obtain an off-white solid (0.29 g, 98% yield). 1H NMR (500 MHz, D2O): δ 3.48 (brs, 2H), 3.01-3.19 (m, 10H), 2.80 (brs, 6H), 2.67 (brs, 2H), 1.84 (brs, 4H); 13C NMR (125 MHz, D2O): δ 179.0, 56.3, 55.7, 48.9, 45.4, 22.8; HRMS (FAB) calculated for C14H28N4O4: 317.2189 [(M+H)+], measured value: 317.2185 [(M+H)+].

Provenance & Evidence