Triacetoxyperiodinane → 3-(11-tert-Butoxycarbonylamino-undecanoylamino)-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester

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Reaction Steps

Composition 15 (56 mg, 0.088 mmol) and Dess-Martin periodinane (48 mg, 0.114 mmol, 1.3 equiv) in DCM (2 mL) were added to a dry round bottom flask equipped with a magnetic stir bar. The cloudy white suspension was allowed to react for 20 minutes. Saturated NaHCO3 (20 ml) was added and the reaction was extracted with EtOAc (20 mL). The organic layer was dried over NaHCO3, concentrated in vacuo, and purified via column chromatography (silica gel, 1:1, hexanes/EtOAc) to give 16 (23 mg, 0.036 mmol, 64% yield) as a sticky white solid. ESMS: 635.4 (M+H+), 657.2 (M+Na+).

Provenance & Evidence