Sodium Thiosulfate → HCID 68709273, compound

Participants

Reaction Steps

4-[(2S*,3S*)-8-methoxy-3-methyl-2,3-dihydro-1,4-benzoxathiin-2-yl]phenol synthesized in Reference Example 14 was dissolved in a mixed solvent of methanol (12 mL) and chloroform (6 mL), and with cooling with ice, a methanol (6 mL) solution of phenyltrimethylammonium tribromide (304 mg) was dropwise added over 5 minutes, and thereafter with cooling with ice, this was stirred for 1.5 hours. Aqueous saturated sodium thiosulfate solution (4 mL) and aqueous saturated sodium hydrogencarbonate solution (4 mL) were added, and then immediately back-extracted twice with chloroform. The organic layer was collected, washed with saturated saline, dried with magnesium sulfate, and the solvent was evaporated off under reduced pressure. The obtained residue was purified by reversed-phase HPLC (0.1% TFA acetonitrile/H2O=10% to 95%, gradient) to obtain the entitled compound (146 mg, 52%) as a white solid.

Provenance & Evidence