Benzyl Alcohol → Benzyl [({3-[(4r)-4-(3,3-dimethylbutyl)-1-hydroxy-4-methyl-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-7-yl}methyl)amino]sulfonylcarbamate

Participants

Reaction Steps

A solution of chlorosulfonylisocyanate (9 μL, 0.1 mmol) in 1 mL of dichloromethane was treated with benzyl alcohol (10 μL, 0.9 mmol), stirred for 30 minutes, treated with a solution of Example 186B (36 mg, 0.07 mmol) and triethylamine (40 μL, 0.3 mmol) in 1 mL of dichloromethane, stirred for 1.5 h, diluted with dichloromethane, washed with 1 N aqueous HCl and water, and concentrated in vacuo. The crude material was purified by chromatography on silica gel with a gradient of methanol in dichloromethane (0-3%) to afford the title compound (34 mg, 67%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.40 (td, J=12.9, 3.7 Hz, 1H), 0.72 (s, 9H), 0.81 (td, J=12.8, 4.6 Hz, 1H), 1.54 (s, 3H), 2.04 (m, 1H), 2.20 (m, 1H), 4.27 (d, J=5.5 Hz, 2H), 5.17 (s, 2H), 7.19 (s, 1H), 7.37 (m, 5H), 7.49 (m, 1H), 7.62 (s, 1H), 7.70 (d, J=3.7 Hz, 2H), 8.11 (d, J=7.7 Hz, 1H), 8.55 (t, J=6.3 Hz, 1H), 11.52 (s, 1H), 14.44 (s, 1H); MS (APCI−) m/z 685 (M−H)−, m/z 472 (M−[SO2NHCbz]−H)—.

Provenance & Evidence