Metaperiodic acid → (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)acetic acid

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 (0.80 mL) was added to a solution of (S)-2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)ethanol (3J) (51.7 mg, 0.14 mmol) in wet acetonitrile (2.0 mL), 0.75% H2O) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C. and quenched with 1.5 M K2HPO4 solution. Ethyl acetate was added and organic layer separated and washed with 1:1 brine/H2O (2×), then saturated NaHSO3/brine. The organic layer was dried (MgSO4), filtered and concentrated and purified by reverse phase HPLC (Gemini, 50 to 95% ACN/H2O+0.1% TFA) and the product lyophilized to give 3K as a white powder (27.8 mg). 1H-NMR: 300 MHz, (CDCl3) δ 7.73 (d, J=7.8 Hz, 1H), 7.64 (s, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.50-7.38 (m, 3H), 7.28-7.22 (m, 3H), 5.25 (s, 1H), 2.54 (s, 3 H), 0.98 (s, 9H). LCMS-ESI− (m/z): [M−H]− calcd for C23H22ClO3: 381.88. Found: 380.9, 382.9.

Provenance & Evidence