Water → HCID 71062432, compound

Participants

Reaction Steps

To a solution of 4-(1-(4-(allyloxy)phenyl)-5-butyl-3-(hydroxymethyl)-1H-pyrazol-4-yl)-N-(naphthalen-2-ylsulfonyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzamide (Example 246, 30 mg, 0.040 mmol) in tert-BuOH (1 mL), THF (0.3 mL), and water (0.1 mL) at 0° C. was added NMO (5.6 mg, 0.048 mmol) followed by osmium tetroxide (0.062 mL, 7.9 mmol, 4 wt %). After stirring at room temperature overnight, the reaction mixture was diluted with EtOAc, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (Isco 40 g column eluting with 0-15% methanol/DCM). The resulting solid was lyophilized from acetonitrile/water to give the title compound (22 mg, 70%) as a white solid. 1H NMR (CD3OD, 1:1 mixture of amide rotamers) δ 8.62 (s, 1H), 8.14-7.93 (m, 6H), 7.64-7.57 (m, 2H), 7.40-6.87 (m, 9H), 4.87-4.00 (m, 9H), 3.70-3.67 (m, 2H), 3.12-2.35 (m, 4H), 1.07-0.88 (m, 4H), 0.56-0.52 (m, 3H); MS(ESI+) m/z 789.5 (M+H).

Provenance & Evidence