Acetyl chloride → L-Xylopyranoside, methyl 5-C-[4-chloro-3-[(2,3-dihydro-1,4-benzodioxin-6-yl)methyl]phenyl]-, (5S)-

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Reaction Steps

A solution of 0.35M HCl in CH3OH was prepared by adding AcCl (25 μL, 0.35 mmol) to CH3OH (1.0 mL) at 0° C., and stirring for 15 min. Compound 136 (50 mg, 0.11 mmol) was treated with this solution for 2 h at 80° C. in a sealed vial. The reaction mixture cooled to room temperature, and quenched with K2CO3 until basic. The mixture was diluted with CH2Cl2, filtered, and concentrated in vacuo. The crude was purified by preparative HPLC (reverse phase) to provide the title compound (22 mg, 48%) as a white solid.

Provenance & Evidence