Acetic Acid → HCID 85472068, compound

Participants

Reaction Steps

To a mixture of Example 12D trifluoroacetate salt (60 mg), triethylamine (0.06 mL, 0.422 mmol) and acetic acid (42 mg, 0.703 mmol) in dichloromethane (2 mL) was added 2,3-dihydroxypropanal (25.3 mg, 0.281 mmol) and MP-cyanoborohydride (224 mg, 0.563 mmol) and the mixture was stirred at room temperature for 2 days. The solid was filtered and rinsed with 10 mL 50% methanol/dichloromethane. The filtrate was concentrated and purified by reverse-phase HPLC (Phenomenex Luna C8 AXIA column, 100 Å), eluting with a gradient of 10-95% acetonitrile/0.1% trifluoroacetic acid in water with 10 mM ammonium acetate to afford the title compound. 1H NMR (400 MHz, dimethylsulfoxide-d6) δ 1.65-1.79 (m, 2 H) 1.91-1.98 (m, 2 H) 2.12-2.25 (m, 2 H) 2.29-2.43 (m, 2 H) 2.65-2.76 (m, 1 H) 2.95-3.05 (m, 2 H) 3.33-3.46 (m, 2 H) 3.60-3.71 (m, 1 H) 5.67 (s, 2 H) 6.11 (s, 1 H) 7.09 (d, J=4.88 Hz, 1 H) 7.57 (dd, J=8.54, 1.53 Hz, 1 H) 7.61-7.68 (m, 1 H) 7.75-7.86 (m, 2 H) 8.15 (d, J=4.88 Hz, 1 H) 8.42 (s, 1 H) 8.46-8.51 (m, 2 H) 11.29 (s, 1 H). MS (ESI) m/e 501 (M+H)+.

Provenance & Evidence