反应详情

To 25 mL round bottom flask charged with acid 101i (97 mg, 0.16 mmol), diisopropyethylamine (0.08 mL, 0.48 mmol) in DMF (5 mL) was added (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (84 mg, 0.19 mmol). After the reaction was stirred at room temperature for 2 h, H2O (5 mL) and EtOAc (10 mL) were added. The organic phase was extracted with aqueous HCl (1M, 2×5 mL), H2O (5 mL), aqueous Na2CO3 (1M, 5 mL), brine (5 mL), dried with Na2SO4 and concentrated. The residue was chromatographed (gradient, 0%-100% 60:35:5 CH2Cl2:Et2O:MeOH/CH2Cl2) to afford 45 mg (48%) of 101. MH+(m/z): 591.5. 1H NMR (300 MHz, CDCl3) 6 m; 8.44 (s, 1 H), 8.39 (m, 1 H), 7.88 (s, 1 H), 7.82 (s, 1 H), 7.39-7.49 (m, 5 H), 7.31-7.35 (, 2 H), 7.07 (d, J=7.5 Hz, 1 H), 6.81 (s, 1 H), 6.58 (d, J=7.5 Hz, 1 H), 3.69 (broad s, 6 H), 3.62 (s, 3 H), 3.07 (m, 1 H), 2.21 (s, 3 H), 1.35 (s, 3 H), 1.33 (s, 3 H); MS (ESI+) m/z (M+H) 590.58.

1. extractionThe organic phase was extracted with aqueous HCl (1M, 2×5 mL), H2O (5 mL), aqueous Na2CO3 (1M, 5 mL), brine (5 mL)
2. dry with materialdried with Na2SO4
3. concentrationconcentrated
4. customThe residue was chromatographed (gradient, 0%-100% 60:35:5 CH2Cl2:Et2O:MeOH/CH2Cl2)