Potassium Carbonate → HCID 86649573, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl N-{[5-(3-[(1S)-2-methoxy-1-methoxyethoxy]-5-{[5-(methylsulfonyl)pyrazin-2-yl]oxy}phenyl)-1H-pyrrol-2-yl]carbonyl}-L-threoninate (13.5 g, 21.2 mmol) synthesized in Example (103b) was dissolved in methylene chloride (150 mL), and cooled to −78° C. Bis(2-methoxyethyl)amino sulfur trifluoride (5.47 mL, 29.7 mmol) was added dropwise, and stirring was carried out at −78° C. for 40 minutes. Potassium carbonate (5.86 g, 42.4 mmol) was added, and stirring was carried out for 1.5 hours with the temperature being raised gradually to room temperature. A saturated aqueous sodium hydrogencarbonate solution (100 mL) was added at 0° C., and extraction was carried out twice with methylene chloride (100 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=40%-70%) to afford the desired product (9.68 g, yield 74%) as a white solid.

Provenance & Evidence