Triacetoxyperiodinane → HCID 89717631, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoro-1-hydroxyethyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (0.200 g, 0.304 mmol) and Dess-Martin periodinane reagent (0.567 g, 1.336 mmol) in DCM (7.50 mL) were stirred at 20° C. for one hour. After evaporation to dryness, the residue was purified by flash chromatography to afford methyl 4-((3-((3-((tert-butoxycarbonyl)amino)propyl)(methyl)amino)propyl)amino)-2-(3-(2,2,2-trifluoroacetyl)benzyl)-9H-pyrimido[4,5-b]indole-7-carboxylate (181 mg, 91% yield) as a yellow foam: 1H NMR in DMSO-d6 is consistent with the desired product but complicated due to presence of hydrate form: MS m/z 657.3 (M+H)+; HPLC 96.0% @ 220 nm and 95.3% @ 254 nm, RT 1.87 and 1.96 (ketone+hydrate) minutes.

Provenance & Evidence