p-Acetamidobenzoic acid → HCID 59784111, compound

Participants

Reaction Steps

Intermediate 7 (191 mg, 0.351 mmol) is dissolved in DMF (10 mL), to which is added DIEA (0.305 mL, 1.75 mmol). This mixture is stirred at room temperature for 0.5 h. 4-Acetamidobenzoic acid (66 mg, 0.368 mmol) is added, and stirring is continued for continued 1 h. HOBt (52 mg, 0.385 mmol) and HBTU (146 mg, 0.385 mmol) are then added and the entire mixture is stirred at room temperature for 2 h. The reaction mixture is diluted with EtOAc (100 mL) and washed sequentially with 1 M citric acid, brine, sat. NaHCO3, brine, water and brine. The EtOAc layer is then dried with MgSO4, filtered, and the solvent removed at room temperature under reduced pressure to afford a colorless gum. This material is purified by flash chromatography on silica gel (EtOAc) to give the title compound as a white foam (211 mg, 85% yield): 1H NMR δ (CDCl3) 6.40-7.62 (m, 11H), 4.25-5.30 (m, 5H), 3.93 (“br d”, 1H, Jobs=11.9 Hz), 3.47 (“br id”, 1H, Jobs=11.4, 3 Hz), 2.65-3.30 (br m, 7H), 1.70-2.22 (br m, 8H), 1.48 and 1.46 (s, 9H total), 1.28-1.34 (m, 3H), 0.60-1.12 (br m, 7H); LCMS (APCl+) 706.7 (MH+, 100%).

Provenance & Evidence