Reaction Steps
By the method described in Example 2, the product of Example 6 (640 mg, 1.24 mmol), ethanethiol (0.45 mL, 6.18 mmol), and aluminum chloride (1.16 g, 8.70 mmol) were stirred in anhydrous CH2Cl2 (20 mL). After chromatography (silica gel, 5-10% methznol in CH2Cl2), the remnant crystallized from MeOH/CH2Cl2 to give 386 mg (64%) of the title product as a yellow solid: 1H NMR (DMSO-d6) d 1.34 (m, 2H), 1.44 (m, 4H), 2.37 (m, 4H), 2.60 (t, J=5.7 Hz, 2H), 4.05 (t, J=5.7 Hz, 2H), 6.64 (d, J=8.3 Hz, 1H), 6.82 (dd, J=2.1 Hz, 8.8 Hz, 1H), 6.89 (d, J=8.8 Hz, 2H), 6.96 (dd, J=2.1 Hz, 8.3 Hz, 1H), 7.05 (d, J=1.8 Hz, 1H), 7.22 (d, J=8.8 Hz, 1H), 7.30 (d, J=1.8 Hz, 1H), 7.61 (d, J=8.8 Hz, 2H), 9.62 (br s, 1H), 9.75 (br s, 1 H); 13C NMR (DMSO-d6) d 15.7, 23.8, 25.4, 54.2, 57.0, 65.9, 107.0, 114.4, 114.8, 115.1, 123.2, 123.6, 124.3, 126.9, 129.5, 129.7, 130.6, 131.6 , 132.3, 139.1, 140.5, 155.3, 155.9, 162.7, 192.6; MS (FD) m/e 487 (M+); Anal. calc'd. for C29H29NO4S: C, 71.43; H, 6.00; N, 2.87. Found: C, 71.33; H, 6.05; N, 2.92.
