Methanesulfonic Acid → HCID 71110534, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the crude alcohol (4.46 g, 5.79 mmol) in THF (50 mL) were added CH3SO3H (0.6 N in MeOH, 18 mL, 10.4 mmol) at −78° C. The mixture was allowed to slowly warm to −30° C. To a mixture was added aq. saturated NaHCO3 solution (50 mL) to quench the reaction. After dilution with water, the mixture was stirred at room temperature for 30 min and extracted with EtOAc (100 mL×2). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude (3R,4S,5S,6R)-2-(4-chloro-5-(4-ethoxybenzyl)-2-methyl-2,3-dihydrobenzofuran-7-yl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (2.52 g) was carried on to the next step without further purification. To a solution of the triol compound (2.52 g) in CH2Cl2/CH3CN (25 mL/25 mL) were added triethylsilane (1.7 mL, 10.2 mmol) and boron trifluoride diethyl etherate (1.3 mL, 10.2 mmol) at −60° C. The mixture was allowed to slowly warm to −10° C. To a mixture was added aq. saturated NaHCO3 solution (20 mL) to quench the reaction. The reaction mixture was stirred at r.t. and evaporated in vacuo to remove CH2Cl2 and CH3CN. The mixture was extracted with EtOAc (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified using reverse phase preparative HPLC to provide the title compound E011 (81 mg, 2.8% (3-steps)).

Provenance & Evidence