Triacetoxyperiodinane → HCID 58316934, compound

Participants

Reaction Steps

In a round bottom flask, (3-{[4-chloro-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-hydroxy-methyl}-2,4-difluoro-phenyl)-carbamic acid benzyl ester (34, 311 mg, 0.519 mmol) is dissolved in 35 mL of tetrahydrofuran and Dess-Martin periodinane (242 mg, 0.571 mmol) is added. The resulting mixture is stirred at room temperature, and additional Dess-Martin periodinane is added. After 60 minutes, the reaction is quenched with water and extracted with ethyl acetate. The organic layer is washed with aqueous sodium bicarbonate, then brine, and dried with magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel chromatography eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (35, 152 mg). MS (ESI) [M+H+]+=596.8.

Provenance & Evidence