Reaction Steps
A mixture of 2-(3-{3-[5-benzyloxy-4-(2-chloroacetyl)-2-ethylphenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester (800 mg, 1.27 mmol), 2-benzyl-2-thiopseudourea hydrochloride (313 mg, 1.52 mmol), sodium iodide (77 mg, 0.51 mmol), and potassium carbonate (700 mg, 5.06 mmol) in N,N-dimethylformamide (20 mL) was treated at 80° C. for 6 h. The mixture was cooled, diluted with diethyl ether, and washed once with water. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo. Chromatography (silica gel, 30% ethyl acetate/70% hexane) of the residue provided 376 mg (40%) of the title compound as a yellow amorphous solid. 1H NMR (CDCl3) δ 7.89 (d, J=8 Hz, 1H), 7.36 (m, 9H), 7.20 (m, 5H), 7.21 (d, J=9 Hz, 1H), 7.06 (d, J=8 Hz, 1H), 6.79 (d, J=8 Hz, 1H), 6.67 (d, J=8 Hz, 1H), 6.55 (s, 1H), 6.43 (d, J=8 Hz, 1H), 5.07 (s, 2H), 4.21 (t, J=6 Hz, 2H), 4.18 (t, J=6 Hz, 2H) , 4.10 (s, 2H), 3.83 (s, 3H), 2.63 (m, 4H), 2.31 (quintet, J=6 Hz, 2H), 1.55 (hextet, J=7 Hz, 2H), 1.18 (t, J=8 Hz, 3H), 0.90 (t, J=7 Hz, 3H); TOF MS ES exact mass calculated for C45H47N2O6S (p+1): m/z=743.3155. Found: 743.3142; IR (CHCL3, cm−1) 2963, 1720, 1602, 1453. Anal. Calcd for C45H46N2O6S: C, 72.75; H. 6.24; N, 3.77. Found: C, 72.69; H, 6.17; N, 3.56.
