1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68744537, compound

Participants

Reaction Steps

(S)-3-(4-benzyloxy-3-hydroxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid (1.23 mmol) was dissolved in DMF (5 ml). EDCI (2 mmol) was added followed by HOBT (1 mmol) and methylamine hydrochloride (2 mmol). N,N-Diisopropylethylamine (2 mmol) was added and the solution was stirred at room temperature for 5 hours. The solution was diluted with water and ethyl acetate. The ethyl acetate extract was washed with dil HCl, with water and with brine. Drying (MgSO4) and evaporation gave the crude product which crystallised from ethyl acetate-hexane (1:1). [(S)-2-(4-Benzyloxy-3-hydroxy-phenyl)-1-methylcarbamoyl-ethyl]-carbamic acid tert-butyl ester was obtained as a white solid, 348 mg; HPLC/MS retention time 5.22 min, m/z 401 (MH+).

Provenance & Evidence