Triacetoxyperiodinane → CID 145857679

Participants

Reaction Steps

In a reaction vial, (imino-{5-methylsulfanyl-4-[3′-(2,2,2-trifluoro-1-hydroxy-ethyl)-biphenyl-3-sulfonyl]-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester (30 mg, 0.051 mmol, as prepared in Example 28, step c) and 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (31 mg, 0.072 mmol, Lancaster Synthesis, Windham, N.H.) were dissolved in DCM (2 mL). To that solution, wet DCM (1 mL, 4 μL H2O) was added slowly via a syringe. After 1 hr of stirring at rt, the reaction was evaporated and the residue was partitioned between Et2O (30 mL) and 10% Na2S2O3-saturated NaHCO3 (1:1, 15 mL). The aqueous layer was washed with an additional portion of Et2O. The combined organic washes were dried with MgSO4 and concentrated in vacuo to give 30 mg (quantitative yield) of the title compound that was used without purification. 1H-NMR (CDCl3; 400 MHz) δ 8.28 (br s, 1H), 8.26 (t, 1H, J=1.7 Hz), 8.08–8.13 (m, 1H), 7.99–8.04 (m, 1H), 7.96 (s, 1H), 7.91–7.95 (m, 1H), 7.82–7.86 (m, 1H), 7.62–7.71 (m, 2H), 2.59 (s, 3H), 1.51 (s, 9H). 19F-NMR (CDCl3; 400 MHz) δ −84.93 (s). ESI-MS (m/z) Calcd. for C25H23F3N2O5S3: 487.6 (M+H); found: 487.2.

Provenance & Evidence