Tert-butoxycarbonylalanine → [(S)-1-(6-Fluoro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester

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Reaction Steps

To an ice-cooled mixture of 6-fluoro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylamine=(195 mg, 1.0826 mmol), (S)-2-tert-butoxycarbonylaminopropionic acid (225 mg, 1.19 mmol) and HOAt (147 mg, 1.083 mmol) in DCM (10 mL) was added EDCI HCl (249 mg, 1.3 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 pink gum (270.6 mg, 71%). LCMS (Method J): RT 3.26 min [M+H]+ 352

Provenance & Evidence