Reaction Steps
To a solution of COMPOUND 142 (61 mg, 0.12 mmol) in toluene (1 mL) was added phosgene (20% in toluene, 82 μL, 0.15 mmol) and the resultant slurry was stirred at room temperature for 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in DMF (1 mL). To the solution were added ammonium chloride (33 mg, 0.62 mmol) and DIPEA (120 μL, 0.69 mmol) and the mixture was stirred at room temperature for 17 hours to afford COMPOUND 158 as a white solid (24 mg, 36%) following work-up and purification. 1H NMR (CDCl3) δ 1.00-1.15 (m, 5H), 1.55 (m, 1H), 1.71 (m, 3H), 2.16 (m, 1H), 2.30 (s, 6H), 2.56 (m, 1H), 2.75-2.87 (m, 3H), 3.29 (m, 1H), 3.57 (m, 1H), 3.79-3.90 (m, 3H), 4.63 (s, 2H), 6.41 (s, 1H), 6.50 (d, 2H, J=7.8 Hz), 6.92-7.04 (m, 5H), 7.43 (s, 3H), 7.52 (br s, 1H), 8.38 (br s, 1H). 13C NMR (CDCl3) δ 13.81, 19.54, 29.41, 30.68, 31.30, 40.24, 43.99, 48.69, 52.49, 57.30, 60.85, 112.86, 114.97, 119.39, 125.05, 127.70, 128.84, 129.63, 130.41, 130.90, 131.39, 134.47, 138.87, 142.42, 146.09, 158.05, 170.39. ES-MS m/z 553 (M+H). Anal. Calcd. for C33H40N6O2.0.85CH2Cl2.0.1C6H14: C, 65.31; H, 6.86; N, 13.27. Found. C, 65.38; H, 6.66; N, 13.07.
