Sodium Iodide → HCID 22103664, compound

Participants

Reaction Steps

To a solution of the title compound of Step (A) (0.2 g, 0.327 mmol) in 4 mL of acetonitrile, chlorotrimethylsilane (0.213 g, 1.1 mmol) and sodium iodide (0.294 g, 1.965 mmol) were added the mixture stirred at room temperature for 30 min. Additional portions of chlorotrimethylsilane (0.12 g, 1.84 mmol) and sodium iodide (0.2 g, 1.33 mmol) were added over a 1 hr period and the mixture stirred for an additional 1 hr. The mixture was diluted with 25 mL of water and 1 mL of saturated aqueous sodium thiosulfate was added and the mixture was then extracted with 3×25 mL of EtOAc. The combined organic extracts were then washed once with water and dried and evaporated. The residue was purified by reverse phase preparative HPLC on a 30×500 mm ODS S10 column using 68% solvent B (90% MeOH, 10% H2O, 0.1% TFA) and 32% solvent A (10% MeOH, 90% H2O, 0.1% TFA). The appropriate fractions were collected and neutralized with aqueous sodium bicarbonate to pH 7 and concentrated to 10 mL. The solution was then acidified to pH 4 using aqueous sodium bisulfate and the white solid was filtered and dried to provide 0.069 g (40%) of the title compound of this Example as a white solid. m.p. 95°-100° C.

Provenance & Evidence