Acetic Acid → HCID 135896314, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of the product of Example 119 (0.4 g, 0.62 mmol) in dichloroethane (6 mL) was added N,N-diisopropylethylamine (0.22 mL, 1.23 mmol). The mixture was stirred at room temperature until homogenous before 2,6-dimethylbenzaldehyde (0.17 g, 1.23 mmol) and MgSO4 (0.15 g) were added. The reaction mixture was heated at 50° C. for 18 h, cooled to room temperature and filtered. To the filtrate was added sodium triacetoxyborohydride (0.21 g, 0.99 mmol) and glacial acetic acid (0.11 mL, 1.86 mmol), and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was diluted with CH2Cl2 (25 mL) and washed with distilled H2O (2×10 mL), dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (1% to 3% MeOH/CH2Cl2 gradient) afforded the title compound as a light orange solid (0.22 g, 40%). 1H NMR (300 MHz, DMSO-D6) δ ppm 13.96 (s, 1H), 9.98 (s, 1H), 8.23 (d, J=7.72 Hz, 1H), 8.03 (d, J=7.72 Hz, 1H), 7.70-7.79 (m, 1H), 7.64 (t, J=7.35 Hz, 1H), 7.45-7.55 (m, 2H), 7.32-7.42 (m, 1H), 7.14-7.22 (m, 1H), 7.04-7.10 (m, 2H), 3.64-3.79 (m, 1H), 3.38-3.43 (m, 1H), 3.02 (s, 3H), 2.31-2.43 (m, 1H), 2.27 (s, 6H), 1.99-2.12 (m, 1H), 0.94-1.12 (m, 1H), 0.68 (s, 9H), 0.32-0.48 (m, 1H); MS m/z 651.3 (M+H)+.

Provenance & Evidence