Potassium Carbonate → HCID 18697443, compound

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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 0.5M KOH (100 mL). The aqueous layer was extracted with ethyl acetate (1x 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 C33 H52N2O4S2). Nuclear magnetic resonance characterization experiments yielded the following molecular signature:

Provenance & Evidence