Triethylamine → Hexamethylenetetramine

Participants

Reaction Steps

C4 (197 mg, 0.201 mmol), EDC hydrochloride (77 mg, 0.401 mmol) and N-hydroxysuccinimide (35 mg, 0.301 mmol) were dissolved in anhydrous dichloromethane (30 ml) and activated ester formation left at room temperature for two hours under argon. To the solution was added E4 (300 mg, 0.211 mmol) and triethylamine (61 mg, 0.602 mmol) and the reaction left overnight at room temperature under argon. The solvents were removed, and the resulting residues purified by gradient silica column chromatography (3-7% methanol in dichloromethane) to yield the title compound as a colourless solid (378 mg, 78%). C119H209N11O37 requires 2384.5. Found ES+: MH22+, 1193.9, MH33+, 796.4. δH (CDCl3) 1.23 (46H, (CH2)19(CH2)2CO, (CH2)4CH), 1.44 (72H, br+m, (Me)3C, CH2CH2N, CH2CH2CO), 1.95 (1H, br, CH), 2.02-2.23 (30H, 10×s, MeCO), 2.17 (2H, t, (CH2)22CH2CO), 2.4-2.8 (4H, brm, CO(CH2)2CO), 2.83 (6H, s, MeN), 2.9-3.5 (32H, m, CH2N), 4.12 (2H, m, CH2OAc), 4.30 (2H, dt, CH2OAc), 5.20, 5.25 (2H, 2×d, CHOAcCO), 5.43, 5.60 (4H, 2×m, (CHOAc)2CHOAcCO), 5.71 (1H, br, (CH2)23CONH), 6.11 (1H, br, CO(CH2)2CONH), 7.18, 7.65 (2H, 2×t, N(CH2CH2NH)2.

Provenance & Evidence