Diisopropylethylamine → (S)-2-tert-Butoxycarbonylamino-3-[4-(3-cyano[1,6]naphthyridin-2-ylamino)phenyl]propionic acid methyl ester

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A solution of (S)-3-(4-Aminophenyl)-2-tert-butoxycarbonylaminopropionic acid methyl ester (0.25 g, 0.84 mmol), 2-chloro[1,6]naphthyridine-3-carbonitrile (0.15 g, 0.77 mmol) (prepared according to the method of E. M. Hawes et al., J. Med. Chem. 1973,16, 849) and diisopropylethylamine (0.11 g, 0.84 mmol) in EtOH (1 ml) were heated under reflux for 3 h. The solvent was removed under reduced pressure and the resulting crude was purified by flash chromatography (CH2Cl2;AcOEt, 1:1) to yield (S)-2-tert-Butoxycarbonylamino-3-[4-(3-cyano[1,6]naphthyridin-2-ylamino)phenyl]propionic acid methyl ester (0.12 g, 34%) as a yellow solid.

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