Hydrochloric Acid → HCID 178457305, compound

Participants

Reaction Steps

4.0 M HCl solution in dioxane (1.0 mL, 4.0 mmol) was added to a solution of compound 20 (87 mg, 0.2 mmol) in dioxane (10 mL) and the reaction mixture was stirred at room temperature for 2 hours. Solvent was evaporated in vacuo and the residue was used directly for the next step without further purification. To a solution of the residue in THF (20 mL) were added cinnamic acid (29 mg, 0.2 mmol), EDCI (38 mg, 0.2 mmol), HOBT (27 mg, 0.2 mmol), and DIPEA (103 mg, 0.8 mmol). The reaction mixture was stirred at room temperature for 2 hours. Solvent was evaporated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, and dried over anhydrous Na2SO4. Flash column chromatography (MeOH/EtOAc, 1:6) gave compound 12 as a colorless oil (75 mg, 80%). 1H NMR (CDCl3, 300 MHz) δ 7.63 (d, J=15.6 Hz, 1H, 7.52-7.35 (m, 5H), 6.39 (d, J=15.6 Hz, 1H), 5.60 (s, broad, 1H), 4.90 (s, 2H), 3.95-3.80 (m, 1H), 3.30-2.30 (m, 8H), 2.20-1.95 (m, 3H), 1.93-1.02 (m, 13H), 0.92 (t, J=6.6 Hz, 3H); 13C NMR (CDCl3, 75 MHz) δ 165.87, 165.05, 144.85, 140.66, 134.92, 129.54, 128.77, 127.73, 121.10, 69.73, 57.86, 52.54, 48.71, 35.18, 33.06, 31.80, 30.84, 26.34, 25.36, 24.76, 18.88, 11.79; HRMS-Electrospray (m/z): [M+H]+ calcd 467.2845. found 467.2830; purity HPLC 95.4%, tR=29.227 min.

Provenance & Evidence