Triethylamine → HCID 135885187, compound

Participants

Reaction Steps

To a solution of product of Example 74D (1.16 g, 2.33 mmol) in dichloromethane (20 mL) was added triethylamine (1.6 mL, 11.7 mmol) followed by dropwise addition of methanesulfonyl chloride (0.45 mL, 5.84 mmol). The reaction mixture was stirred at room temperature for 18 h. The solution was diluted with ethyl acetate (30 mL), washed with aqueous 1 N HCl (2×15 mL), dried (Na2SO4), and concentrated in vacuo. The resulting residue was taken up in methanol (20 mL) and treated with excess K2CO3 for 2 h. The mixture was filtered. The filtrate was concentrated in vacuo and the resulting residue was taken up in 3:1 dichloromethane:isopropanol (15 mL) and washed with aqueous 1 N HCl (2×10 mL), dried (Na2SO4), and concentrated in vacuo to afford the title compound as a light yellow solid (1.1 g, 82%). 1H NMR (500 MHz, DMSO-d6), δ ppm 0.44-0.54 (m, 1H), 0.66 (s, 9H), 0.87-0.98 (m, 1H), 1.80-1.89 (m, 4H), 1.95-2.05 (m, 1H), 3.08 (s, 3H), 7.53 (t, J=7.25 Hz, 2H), 7.58 (dd, J=8.69, 2.32 Hz, 1H), 7.64 (d, J=2.32 Hz, 1H), 7.70-7.78 (m, 2H), 8.12 (d, J=7.54 Hz, 1H), 9.14 (s, 1H), 10.24 (s, 1H), 13.61 (s, 1H); MS m/z 575.2 (M+H)+.

Provenance & Evidence