Hydrochloric Acid → HCID 135885173, compound

Participants

Reaction Steps

A mixture of the product of Example 39A (16 mg, 0.026 mmol) and 4 N HCl in dioxane (0.26 mL) was stirred at room temperature for 4 h and then concentrated in vacuo. The resulting residue was taken up in dichloromethane (1 mL) and triethylamine (36 μL, 0.3 mmol) and methanesulfonyl chloride (10μL, 0.13 mmol) were then added. The reaction solution was stirred at room temperature for 2 h. The solution was then washed with aqueous 1 N HCl (2×0.5 mL), dried (Na2SO4), and concentrated in vacuo. The residue was then dissolved in methanol (1 mL) and treated with excess of K2CO3 for 30 min. The mixture was diluted with ethyl acetate (3 mL) and filtered. The filtrate was washed with aqueous 1 N HCl (2×1 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (1%→3%→5% methanol/dichloromethane) afforded the title compound as a yellow solid (8 mg, 53%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.38-0.56 (m, 1H), 0.60-0.73 (m, 6H), 0.91-1.09 (m, 1H), 1.17-1.39 (m, 2H), 2.01 (s, 3H), 2.11-2.32 (m, 1H), 3.03 (s, 3H), 4.05 (s, 3H), 7.32-7.62 (m, 7H), 8.05 (d, J=7.72 Hz, 1H), 10.05 (s, 1H), 14.46 (s, 1H); MS m/z 591.1 (M+H)+.

Provenance & Evidence