Metaperiodic acid → HCID 68981055, compound

Participants

Reaction Steps

3-Cyano-N-[2-(4-cyanophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]-N-methyl-1-naphthamide acetate (see Example 28; 60 mg, 0.10 mmol) was dissolved in a mixture of acetonitrile (3 mL) and CH2Cl2 (1 mL) and to the resultant solution was added a catalytic amount of FeCl3 with cooling. The mixture was stirred for 5 min and then periodic acid (26 mg, 0.11 mmol) was added whereupon stirring was continued overnight at 0° C. Another catalytic amount of FeCl3 as well as an additional portion of periodic acid (26 mg, 0.11 mmol) was added. The reaction mixture was stirred at 0° C. for 2 h and then quenched by addition of Na2S2O3. The mixture was extracted thrice with CH2Cl2 and the organics washed twice with water and then dried over Na2SO4. The solvent was removed by evaporation and the product was purified by reversed phase chromatography using a mixture of acetonitrile and 0.1 M ammonium acetate aq. There was obtained 25 mg (41%) of the title compound as a pale yellow solid. 1H NMR: (400 MHz, CDCl3): 1.4-2.0 (cm, 3H), 2.0 (s, 3H), 2.1-4.3 (cm, 20H), 6.4-8.0 (cm, 9H), 8.2 (s, 1H); LCMS: m/z 540 (M+1)+.

Provenance & Evidence