Sodium periodate → 3-(4,4-Dibutyl-7-fluoro-1-hydroxy-3-oxo-3,4-dihydronaphthalen-2-yl)-4h-1,2,4-benzothiadiazine-7-carbaldehyde 1,1-dioxide

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Reaction Steps

A solution of the compound of Example 21A (52 mg, 0.10 mmol) in dioxane (2 mL) and water (200 μL) was treated with a solution of osmium tetroxide in t-butanol (2.5% (wt/vol), 200 μL) and sodium periodate (45 mg, 0.21 mmol) followed by stirring at ambient temperature for 24 h. The mixture was diluted with water and saturated ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic layer washed with water and saturated NaCl solution. Drying (Na2SO4) and concentration in vacuo afforded the title compound (47 mg, 90%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 0.51 (m, 2 H) 0.69 (t, J=7.35 Hz, 6 H) 0.90 (m, 2 H) 1.10 (m, 4 H) 1.92 (m, 2 H) 2.15 (m, 2 H) 7.52 (m, 1 H) 7.73 (m, 3 H) 8.11 (dd, J=8.64, 1.65 Hz, 1 H) 8.40 (d, J=1.47 Hz, 1 H) 10.03 (s, 1 H) 14.38 (s, 1 H).

Provenance & Evidence