[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]([NH:17][CH2:18][CH2:19]Cl)=[O:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[H-].[Na+]>O1CCCC1>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:19][CH2:18][NH:17][C:15]2=[O:16])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]A solution of {3-[3-(2-chloro-ethyl)-ureido]-phenyl}-carbamic acid tert-butyl ester (1 g, 3.2 mmol) and potassium carbonate (1.32 g, 9.6 mmol) in dry tetrahydrofuran (20 ml) were stirred at room temperature overnight. No reaction was observed. Sodium hydride (260 mg, 6.5 mmol, 60% dispersion in oil) was then added and reaction stirred at room temperature overnight. Reaction was quenched with water (50 ml) then extracted with dichloromethane (3×50 ml). The combined organics were dried (magnesium sulphate) and concentrated in vacuo. HPLC retention time 7.0 min. Mass spectrum (ES+) m/z 295 (M+NH4)
Loading…
