Metaperiodic acid → Periodic acid chromium trioxide

Participants

Reaction Conditions

Reaction Steps

A stock solution of periodic acid/chromium trioxide was prepared according to WO 99/52850 by dissolving periodic acid (11.4 g, 50.0 mmol) and chromium trioxide (23 mg, 1.2 mol %) in wet acetonitrile (0.75% H2O) to a volume of 114 mL. This stock solution (0.090 mL) was added to a solution of (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)ethanol (5K) (5 mg, 0.013 mmol) in wet acetonitrile (1.0 mL, 0.75% H2O) at 0° C. Reaction mixture was stirred for 0.5 hour at 0° C. Then more stock solution (0.2 ml) was added and the reaction mixture was stirred for 1 h at 0° C. The reaction mixture was filtered and purified by reverse phase HPLC (Gemini, 10 to 95% ACN/H2O+0.1% TFA). Product lyophilized to give a white powder. 1H-NMR: 300 MHz, (CD3OD) δ: 9.06 (s, 1H), 7.78 (s, 1H), 7.57-7.42 (m, 4H), 5.16 (s, 1H), 2.52 (s, 3H), 0.86 (s, 9H). LCMS-ESI+: calc'd for C20H20ClNO3S: 390.0 (M+H+). Found: 390.1 (M+H+).

Provenance & Evidence