[(S)-1-(3-Bromo-2-cyclopropylamino-4-fluorophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(7-Bromo-1-cyclopropyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([Br:19])[C:13]=1[NH:20][CH:21]1[CH2:23][CH2:22]1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([C:10]1[N:20]([CH:21]2[CH2:23][CH2:22]2)[C:13]2[C:14]([Br:19])=[C:15]([F:18])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
[(S)-1-(3-Bromo-2-cyclopropylamino-4-fluoro-phenylcarbamoyl)ethyl]carbamic acid tert-butyl ester (1.05 g, 2.52 mmol) was taken up in AcOH (12 mL) and heated at 70° C. for 16 h. After cooling to RT, the volatiles were evaporated in vacuo and the residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous phase was further extracted with EtOAc and the combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-50% EtOAc in cyclohexane) to afford the title compound (771 mg, 77%) as a yellow oil. LCMS (Method C): RT 3.65 min [M+H]+ 398.09.