1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-(3-Benzyloxycarbonylamino-propionylamino)-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonylethoxymethyl)-propoxy]-propionic acid ethyl ester

Beteiligte Stoffe

Reaktionsschritte

The compound 23 was prepared using General Procedure B with amine 1 (4.0 g, 9.49 mmol), N-Cbz-β-alanine (2.54 g, 11.39 mmol), 1-hydrobenzotriazole (HOBt) (1.53 g, 11.39 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (2.18 g, 11.39 mmol) in CH2Cl2 (50 mL). Purification by flash column chromatography (on silica gel, EtOAc:n-hexane=1:3) afforded 5.36 g (90%) of the desired product 23 as a colorless syrup. 1H NMR (CDCl3): δ 7.31 (m, 5H, ArH), 6.16 (s, 1H, NH), 5.66 (s, 1H, NH), 5.08 (s, 2H, OCH2Ar), 4.12 (q, J=6.4 Hz, 6H, OCH2), 3.67 (m, 12H, CH2O), 3.45 (dt, J=7.4, 15.0 Hz, 2H, CH2NHCO), 2.51 (t, J=8.4 Hz, 6H, CH2CO), 2.37 (dt, J=7.4, 8.6 Hz, 2H CH2CO), 1.24 (t, J=6.4 Hz, 9H, CH3).

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