Methyl chloroformate → HCID 57925939, compound

Participants

Reaction Steps

To a solution of tert-butyl (3-{[4-({[2-(dimethylphosphoryl)ethyl]amino}methyl)benzoyl]amino}biphenyl-4-yl)carbamate (295 mg, 0.566 mmol) in CH2Cl2 (10 mL) were added DIEA (198 μl, 1.13 mmol) and methyl chloroformate (70 mg, 0.735 mmol). After stirring for 30 min at room temperature, the reaction was diluted with CH2Cl2 and washed with saturated NaHCO3. The aqueous layer was extracted with additional CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/CH2Cl2) afforded a colorless solid. This solid was taken up in CH2Cl2 (5 mL) and TFA (1 mL). After stirring at room temperature for 1 h, the solution was diluted with 1,2-DCE and concentrated. The residue was diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (MgSO4), and evaporated to afford the title compound as a pale yellow solid. NMR (DMSO-d6, 600 MHz) δ 9.70 (bs, 1H), 7.96 (d, J=8.1 Hz, 2H), 7.54-7.50 (m, 2H), 7.50-7.48 (m, 1H), 7.37-7.32 (m, 4H), 7.29 (dd, J=8.2, 2.1 Hz, 1H), 7.20 (t, J=7.4 Hz, 1H), 6.83 (d, J=8.5 Hz, 1H), 5.07 (bs, 2H), 4.52 (s, 2H), 3.69-3.57 (m, 3H), 3.45-3.34 (m, 2H), 1.99-1.87 (m, 2H), 1.34 (d, J=12.9 Hz, 6H). MS: cal'd 480 (MH+), exp 480 (MH+).

Provenance & Evidence