Metaperiodic acid → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-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 (0.40 mL) was added to a solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol (10 mg) in wet acetonitrile (1.5 mL, 0.75% H2O) at 0° C. The reaction mixture was stirred for 30 minutes at 0° C. Filtration and purification by reverse phase HPLC (0.1% TFA/CH3CN-0.1% TFA/H2O) gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)acetic acid (7.2 mg). 1H-NMR 400 MHz, (CD3OD) δ 7.76 (m, 2 H), 7.62 (m, 3 H), 7.30 (m, 2 H), 5.14 (s, 1H), 3.89 (m, 8H), 2.66 (s, 3H), 0.97 (s, 9H); LCMS-ESI+ (m/z): [M+H]+ calcd for C26H30ClN2O4: 469.2. Found: 469.3; LCMS-ESI− (m/z): [M−H]− calcd for C26H28ClN2O4: 467.2 Found: 467.0.

Provenance & Evidence