反应详情

(3S, 4R)-4-Amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol [prepared by the method of Quagliato et al. Biorg. and Med. Chem. Let. 1991, 1, 39; (1.00 g, 3.61 mmol)] and the thiadiazole derivative (0.78 g, 3.79 mmol) obtained in Step 1 were stirred together in acetonitrile (15 mL) at 90° C. for 18 hours. The mixture was cooled and concentrated, and the residue was purified by column chromatography (1:1:05 hexane/ethyl acetate/dichloromethane) to give after trituration with hexanes 1.10 g (71%) of product as a white solid: mp 192°-194° C.; 1H NMR (DMSO-D6): δ 9.55 (d, 1H), 7.29 (d, 1H), 7.19 (d, 1H), 6.87 (d, 1H), 5.89 (d, 1H), 4.73 (t, 1H), 4.51 (q, 2H), 3.78 (m, 1H), 1.41 (t, 3 H), 1.38 (s, 3H), 1.15 (s, 3H); IR (KBr): 2500-3250, 1620, 1490 cm-1 ; MS (m/z) 438 (MH+, 100%), 261 (20).

1. temperatureThe mixture was cooled
2. concentrationconcentrated
3. customthe residue was purified by column chromatography (1:1:05 hexane/ethyl acetate/dichloromethane)
4. customto give after trituration with hexanes 1.10 g (71%) of product as a white solid