Reaction Steps
Following the general procedure detailed for 84, 91 (0.029 g, 0.074 mmol, 1 equiv) was treated with Et3N (0.052 mL, 0.371 mmol, 5 equiv) and CH3SO2Cl (0.017 mL, 0.148 mmol, 2 equiv). Radial chromatography (SiO2, 1 mm plate, 50% EtOAc-hexane) furnished 93 (0.032 g, 0.035 g theoretical, 91%) as a white solid: mp 130-132° C.; 1H NMR (500 MHz, CDCl3) major rotamer δ 8.40 (d, J=8.5 Hz, 1H), 8.13 (d, J=8.5 Hz, 1H), 7.61-7.35 (m, 7H), 6.63 (s, 1H), 5.27-5.17 (m, 2H), 4.51-4.33 (m, 4H), 3.60 (s, 3H), 2.86-2.81 (m, 1H), 2.54 (s, 3H), 2.32-2.23 (m, 1H), 2.07-2.04 (m, 1H), 1.76-1.70 (m, 2H); 13C NMR (125 MHz, CDCl3) major rotamer δ 155.3, 153.7, 139.5, 136.6, 133.1, 128.6 (2C), 128.0 (2C), 127.7, 127.6, 127.3, 125.4, 124.3, 123.4, 122.8, 106.9, 71.1, 70.1, 53.0, 48.3, 36.8, 36.2, 26.7, 24.5; IR (film) νmax 3063, 3022, 2938, 2858, 1701, 1593 cm−1; FABHRMS (NBA) m/z 470.1648 (M+H+, C25H27NO6S requires 470.1637).
