Reaction Steps
A solution of the product of Example 1 (0.65 g, 1.25 mmol), ethanethiol (0.46 mL, 6.32 mmol), and aluminum chloride (1.17 g, 8.78 mmol) in anhydrous CH2Cl2 (20 mL) was stirred for 3.5 h. The mixture was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicaronate and brine, dried (sodium sulfate), and concentrated. The residue was purified by chromatography (silica gel, 5-10% MeOH in CH2Cl2) and crystallized from MeOH/CH2Cl2 to give 240 mg (39%) of the title product as a yellow solid: 1H NMR (MeOD-d4) d 1.62 (m, 2H), 1.80 (m, 4H), 3.11 (m, 4H), 3.34 (t, J=6.0 Hz, 2H), 4.32 (t, J=6.0 Hz, 2H), 4.86 (br s, 2H), 6.75 t, J=8.6 Hz, 1H), 6.88 (dd, J=2.2 Hz, 8.8 Hz, 1H), 6.92 (d, J=8.8 Hz, 2H), 6.97-7.06 (m, 3H), 7.27 (d, J=2.2 Hz, 1H), 7.43 (d, J=8.8 Hz, 1H), 7.73 (d, J=8.8 Hz, 2H); 13C NMR (DMSO-d6) d 21.8, 23.1, 53.0, 63.4, 107.1, 114.6, 115.4, 115.7, 116.0, 118.1, 123.4, 124.2, 125.0, 130.0, 130.4, 131.8, 131.9, 138.9, 139.3, 145.3, 145.5, 148.9, 152.1, 155.7, 162.0, 192.3; MS (FD) m/e 492 (MH+); Anal. calc'd. for C28H26FNO4S.0.75 H2O: C, 66.57; H, 5.65; N, 2.77. Found: C, 66.68; H, 5.78; N, 2.74.
