Reaction Steps
A concentrated solution of the amine 17 (0.14 g, 0.18 mmol) in ethyl acetate was added cooled to 0° C. A total of 4 mL of a freshly prepared saturated solution of HCl in ethyl acetate was added dropwise and the solution stirred for 1 h at room temperature. The ethyl acetate was removed in vacuo and the residue co-evaporated with ethyl acetate and chloroform to give the product 24 as an off white powder (0.15 g, 98%); 1H NMR (CDCl3) d 7.27 (s, 1H, aryl), 7.00 (d, 1H, aryl), 6.82 (d, 1H, aryl), 5.33 (m, 4H, olefinic), 4.14 (m, 2H, benzylic), 4.01 (t, 2H, OCH2), 3.95 (t, 2H, OCH2), 3.87 (t, 2H, CH2), 3.78 (t, 2H, CH2), 3.70 (t, 4H, CH2), 3.25 (t, 2H, CH2) 2.93 (m, 2H, CH2), 2.02 (m, 8H, CH2C═C), 1.89 (m, 4H, CH2CH2O), 1.53-1.18 (m, 44H, 22×CH2), 0.89 (t, 6H, CH3); 13C NMR (300 MHz, CDCl3) d 149.91, 149.62, 130.12, 130.00, 123.28, 122.61, 115.46, 113.63, 70.22, 70.09, 69.64, 69.40, 66.50, 65.98, 51.06, 45.08, 40.11, 32.28, 30.15, 29.92, 29.70, 27.60, 26.54, 26.43, 23.07, 14.54; HRMS (FAB): theory for C49H91N2O4 (M+1), 771.6973; found (M+1), 771.6967; Anal. (C49H92Cl2N2O4.0.4H2O): C, H, N.
