Methyl iodide → HCID 59376452, compound

Participants

Reaction Steps

To a solution of tert-butyl [2-({-4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate (41 mg, 0.073 mmol) in THF (1 mL) at room temperature was added potassium tert-butoxide (85 μL, 1 M in THF, 0.085 mmol). The solution was stirred for 30 min and methyl iodide (6 μL, 0.096 mmol) was added. The reaction mixture was stirred at room temperature for 4 h, diluted with ethyl acetate, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (20% to 65% ethyl acetate in hexanes) gave tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-1-methyl-2-oxoethyl]benzoyl}amino)phenyl]carbamate (14 mg, 33%) as a white solid: 1H NMR (600 MHz, CDCl3) δ 9.29 (s br, 1H), 8.93 (s br, 2H), 7.98 (d, J=8.2 Hz, 2H), 7.75 (d, J=7.6 Hz, 1H), 7.52-7.50 (m, 6H), 7.34 (t, J=8.2 Hz, 4H), 7.27 (d, J=7.0 Hz, 1H), 7.21 (td, J=7.9, 1.5 Hz, 1H), 7.17-7.14 (m, 3H), 6.92 (s br, 1H), 2.07 (s, 3H), 1.49 (s, 913); ESIMS calcd 579.3 (M++H), found 579.2 (M++H).

Provenance & Evidence