(4R)-2-[bis(methylthio)methylene]-4-(3,3-dimethylbutyl)-4-methylnaphthalene-1,3(2H,4H)-dione → (1R)-1-(3,3-dimethylbutyl)-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-1-methylnaphthalen-2(1H)-one

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Reaction Steps

A solution of the product of Example 10E (2.02 g, 7.9 mmol) and the product of Example 49E (2.49 g, 6.9 mmol) in 200 mL of toluene was warmed to reflux for 5 h, cooled, and concentrated in vacuo. The crude material was chromatographed on silica gel with methanol/dichloromethane (1:99) to afford the title compound (3.03 g, 85% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.39 (td, J=12.59, 3.13 Hz, 1 H) 0.72 (s, 9 H) 0.82 (m, 1 H) 1.57 (s, 3 H) 2.04 (m, 1 H) 2.22 (td, J=12.69, 4.41 Hz, 1 H) 3.33 (s, 3 H) 4.63 (s, 2 H) 4.71 (s, 2 H) 7.40 (s, 1 H) 7.53 (m, 1 H) 7.74 (d, J=4.04 Hz, 2 H) 8.13 (d, J=7.72 Hz, 1 H) 14.00 (s, 1 H); MS (APCI−) m/z 517 (M−H)−; Analysis calc'd for (C25H30N2O6S2): C, 57.89; H, 5.83; N, 5.40. Found: C, 57.82; H, 6.12; N, 5.05.

Provenance & Evidence