Trimethylsilyldiazomethane → HCID 46229265, compound

Participants

Reaction Steps

To a solution of (2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-hydroxy-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (100 mg, 0.26 mmol) from step 2 in dichloromethane (8 mL) and methanol (2 mL) at 0° C. was added (trimethylsilyl)diazomethane (2.0 M in diethyl ether, 0.65 mL, 1.3 mmol). The reaction mixture was stirred with gradual warming to ambient temperature over 1 h and concentrated in vacuo. Purification by reverse phase preparative HPLC (Gilson®, SunFire™ Prep, 5 to 50% acetonitrile in water gradient) provided the title compound (69 mg, 0.17 mmol, 66%) as a yellow solid.

Provenance & Evidence