Triacetoxyperiodinane → N-[(1,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-oxo-5-(2'6'-dichlorobenzyloxy)pentanoic Acid, T-Butyl Ester

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Reaction Steps

Dess-Martin periodinane (195 mg) was added as a solid to a solution of N-[(2,3-dimethylindole-2-carbonyl)valinyl]-3-amino-4-hydroxy-5-(2′,6′-dichlorobenzyloxy)pentanoic acid, t-butyl ester (96 mg) in DMSO (1.5 ml). The resulting solution was stirred under a nitrogen atmosphere at room temperature for thirty minutes, hen partitioned between EtOAc and water. The organic phase was washed with water 2×) and brine, dried (Na2SO4), and concentrated to give a white solid (83 mg). Flash chromatographic purification with EtOAc/hexanes (1:1) afforded the title product as a white solid (54 mg). TLC (EtOAc/hexanes; 1:1, silica gel): Rf=0.52.

Provenance & Evidence