Acetic Acid → HCID 135475794, compound

Participants

Reaction Steps

To a solution of Example 83B (100 mg, 0.18 mmol) in dichloromethane (2.5 mL) was added benzaldehyde (23 μL, 0.22 mmol), acetic acid (26 μL, 0.46 mmol) and sodium triacetoxyborohydride (63 mg, 0.30 mmol) and the solution was stirred at room temperature for 16 hours. 10% NaHCO3 (10 mL) was added and the solution stirred for 10 minutes, diluted with H2O (10 mL) and the solution extracted with dichloromethane (3×10 mL). The organic extracts were combined, dried (Na2SO4), the drying agent filtered off and the solvent removed in vacuo to give a crude residue which was purified by column chromatography on silica gel (2% methanol/chloroform). The pure material was dissolved in 4M HCl in dioxane (4 mL) and the solution stirred at room temperature for 3 hours, solvent removed in vacuo and the residue dissolved in dichloromethane (4 mL). To this solution was added pyridine (56 uL, 0.9 mmol) and methanesulfonyl chloride (13 μL, 0.22 mmol) and the solution stirred at room temperature for 48 hours, solvent was removed in vacuo and the crude residue was purified by column chromatography on silica gel 4-6% methanol/chloroform) to give the title compound as a colorless solid (75 mg, 67%); 1H NMR (d6-DMSO) δ 14.00 (s, 1H), 9.98 (s, 1H), 8.21, 8.19 (d, 1H), 7.94, 7.92 (d, 1H), 7.77-7.27 (m, 10H), 3.02 (s, 3H), 2.35-2.17 (m, 1H), 2.05-1.89 (m, 1H), 1.36-1.21 (m, 1H), 0.73-0.61 (q, 6H), 0.58-0.45 (m, 1H); MS (ESI) m/z 609 (M+H+).

Provenance & Evidence