Water → HCID 22103720, compound

Participants

Reaction Steps

To a solution of the title compound of Step (A) in 4 ml of CH3CN, Me3SiCl (174 mg, 1.6 mmol) was added and followed by NaI (240 mg, 1.6 mmol). The mixture was stirred at room temperature for 20 min. Additional Me3SiCl (74 mg, 1.6 mmol) and NaI (240 mg, 1.6 mmol) were added in four portions and the reaction was stirred for additional 1 hr and 10 min. The reaction mixture was then added to 3 ml H2O and 30 ml EtOAc. The organic layer was separated and washed with 1 ml saturated aqueous Na2S2O3, brine, dried and concentrated. The residue was purified by preparative HPLC on an ODS S10 column using 30% solvent A (10% MeOH, 90% H2O, 0.1% TFA) and 70% solvent B (90% MeOH, 10% H2O, 0.1% TFA) to provide the title compound of this Example (43 mg, 40% for two steps) as a white solid, m.p. 135°-142° C. (amorphous).

Provenance & Evidence