Triacetoxyperiodinane → HCID 71577130, compound

Participants

Reaction Steps

(2S,4R)-tert-butyl 2-((2S,3S)-1-(cyclopropylamino)-2-hydroxy-1-oxopentan-3-ylcarbamoyl)-4-(2,4-dimethylphenylsulfonyl)pyrrolidine-1-carboxylate (64 mg, 119 μmol, Eq: 1.00) and Dess-Martin periodinane (572 mg, 202 μmol, Eq: 1.7) were combined with CH2Cl2 (1 ml). The reaction was stirred overnight at RT. Dess-Martin periodinane (280 mg) was added again and stirred for 5 h, until near complete conversion. The reaction was extracted with 15 ml CH2Cl2 and 2×5 ml satd. Na2S2O3. The organic layers were dried over Na2SO4 and concentrated in vacuo. The crude material was purified by preparative HPLC. The title compound was obtained as a light yellow gum (52.5 mg, 82.3%, MS (m/e)=536.24 [M+H+]).

Provenance & Evidence