Potassium Carbonate → HCID 18697443, compound

Participants

Reaction Steps

To N,N'-bis-[2-(4-methoxybenzylthio)-2-methylpropyl]-ethylenediamine (4.13 g, 8.66 mmol) in CH3CN (50 mL) was added K2CO3 (1.21 g, 8.75 mmol, 101 mol %) followed by ethyl 5-bromovalerate (2.80 mL, 17.7 mmol, 204 mol %). The reaction was stirred at reflux overnight and was then concentrated to a paste in vacuo. The residue was partitioned between ethyl acetate (100 mL) and 0.5 M KOH (100 mL). The aqueous layer was extracted with ethyl acetate (1×50 mL) and the combined organic layers were washed with NaCl solution (50 mL), dried with Na2SO4 and concentrated to a yellow oil (~6 g). Purification by normal-phase preparative HPLC (100% CHCl3 to 5% methanol/chloroform over 25 min.) afforded pure title compound (1.759 g, 34% yield). FABMS analysis gave an (MH+) of 605 (compared with the value of 604.90 calculated for C33H52N2O4S2). Nuclear magnetic resonance characterization experiments yielded the following molecular signature:

Provenance & Evidence