Ethanol → HCID 54471273, compound

Participants

Reaction Steps

A 250 mL single-necked round-bottomed flask, equipped with stir bar and reflux condenser, was charged with 9-phthalimido-N1 -(t-butoxycarbonyl)-N1, N4 -bis[2-methyl-2-(triphenylmethylthio)propyl ]-1,4-diazanonane (5.50 g, 5.319.43 mmol) in 25 mL of THF. To this was added 100 mL ethanol and 5 mL water. The addition of water caused the starting material to precipitate out of solution. Hydrazine hydrate (1.2 mL, 24.7 mmol, 466 mole %) was added, and the reaction heated at reflux for two days. The reaction mixture was concentrated and partitioned between 100 mL each of water and 0.25M K2CO3. The organic layer was separated and washed once with brine (75 mL), dried over Na2SO4 and concentrated to a solid foam. Purification of the crude product by low-pressure liquid chromatography (100 g SiO2, CHCl3 →5% methanol in CHCl3, the column pre-treated with 200 mL 2% triethylamine in CHCl3) afforded 3.27 g of pure N1 -(t-butoxycarbonyl)-N1,N4 -bis [2-methyl-2-(triphenylmethylthio)propyl ]-1,4,10-triazadecane as a yellow foam (68% yield). Chemical analysis of the purified product confirmed its identity as follows:

Provenance & Evidence