Tert-butoxycarbonylalanine → {1-[6-Fluoro-1-(3-fluoropyridin-2-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester

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Reaction Conditions

Reaction Steps

A mixture of 4-fluoro-N2-(3-fluoropyridin-2-yl)benzene-1,2-diamine (81 mg, 0.37 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (76 mg, 0.40 mmol), HOAt (55 mg, 0.40 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (77 mg, 0.40 mmol) in DCM (5 mL) was stirred at 0° C. for 2 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was dried and concentrated in vacuo. The resulting residue was taken up in AcOH (5 mL) and heated at 70° C. for 24 h. After cooling to RT, the volatiles were removed in vacuo and the resulting residue partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The organic fraction was washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting oil was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc) to afford the title compound as an orange oil (84 mg, 61%). LCMS (Method C): RT 3.28 min [M+H]+ 375.22

Provenance & Evidence