Tert-butoxycarbonylalanine → [(S)-1-(5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

Beteiligte Stoffe

Reaktionsschritte

To an ice-cooled mixture of the 5-fluoro-1,2,3,4-tetrahydroquinolin-8-ylamine and 5-fluoroquinolin-8-ylamine from the previous step (70.4 mg, 0.424 mmol), (S)-2-tert-butoxycarbonylaminopropionic acid (88.3 mg, 0.466 mmol) and HOAt (57.7 mg, 0.424 mmol) in DCM (6 mL) was added EDCI HCl (97.7 mg, 0.51 mmol). The reaction mixture was stirred in the ice bath for 2 h, then diluted with DCM, washed with aqueous Na2CO3 and then water. The organic layer was dried (Na2SO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 20-50% EtOAc in cyclohexane) affording the title compound as a purple gum (105 mg, 73%). LCMS (Method B): RT 3.35 min [M+H]+ 338.

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