Carbamic chloride, N-methyl-N-phenyl- → HCID 59784104, compound

Participants

Reaction Conditions

Reaction Steps

Intermediate 7 (175 mg, 0.322 mmol) is dissolved in anhydrous CH2Cl2 (15 mL), to which DIEA (70 μL, 0.40 mmol) is added. The solution is cooled to 0° C. and N-methyl-N-phenylcarbamoyl chloride (66 mg, 0.39 mmol) is added, the solution is subsequently warmed to room temperature for 4 h. N-Methyl-N-phenylcarbamoyl chloride (66 mg, 0.39 mmol) and DIEA (70 μL, 0.40 mmol) are added and the solution is stirred at room temperature for 15 h at room temperature. The solution is diluted with CH2Cl2 (50 mL) and washed with sat. NaHCO3 and brine. The solution is dried (MgSO4), filtered, and the solvent removed under reduced pressure to give the crude product as an oil. This material is purified by flash chromatography on silica gel (0-5% MeOH/CH2Cl2). The title compound is isolated as a white foam (168 mg, 77% yield): 1H NMR δ (CDCl3) 6.60-7.60 (m, 10H), 4.19-5.20 (m, 5H), 3.62 (“br d”, 1H, Jobs=13.2 Hz), 3.52 (“br d” 1H, Jobs=13.4 Hz), 2.56-3.28 (m, 10H), 1.72-2.10 (m, 5H), 1.47 and 1.45 (s, 9H total), 1.24-1.32 (br m, 3H), 0.88-1.12 (m, 2H), 1.09 (br d, 1H, J=6.7 Hz), 0.90 (dd, 2H, J=7.0, 2.6 Hz), 0.78 (br d, 2H, J=6.7 Hz), 0.66 (br d, 2H, 6.7 Hz; LCMS (APCl+) 678.6 (MH+, 100%).

Provenance & Evidence