Selectfluor → HCID 59376445, compound

Participants

Reaction Steps

tert-Butyl [2-({(4-[2-anilino-1-(anilinocarbonyl)-1-fluoro-2-oxoethyl]benzoyl}amino)phenyl]carbamate. To a solution of tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate (59 mg, 0.10 mmol) in THF (2 mL) at room temperature was added potassium tert-butoxide (110 μL, 1 M in THF, 0.11 mmol). The solution was stirred for 5 min and Selectfluor™ (40 mg, 0.11 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 18 h, diluted with ethyl acetate, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by reverse phase HPLC (30% to 100% MeCN in water) gave tert-butyl [2-({-4-[2-anilino-1-(anilinocarbonyl)-1-fluoro-2-oxoethyl]benzoyl}amino)phenyl]carbamate (11 mg, 18%) as a white solid: 1H NMR (600 MHz, CDCl3) δ 9.42 (s br, 1H), 9.11 (s br, 2H), 8.02 (d, J=8.2 Hz, 2H), 7.86 (d, J=8.5 Hz, 2H), 7.77 (d, J=7.9 Hz, 1H), 7.58 (d, J=7.6 Hz, 4H), 7.37 (t, J=7.6 Hz, 4H), 7.25-7.16 (m, 5H), 6.78 (s br, 1H); ESIMS calcd 605.2 (M++H), found 605.2 (M++Na).

Provenance & Evidence