Methanol → 2-tert-Butoxycarbonylamino-3-(3-aminopyridin-2-ylamino)propionic acid methyl ester

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Reaction Steps

A solution of (2S) 2-tert-Butoxycarbonylamino-3-(3-aminopyridin-2-ylamino)-propionic acid (360 mg, 1.21 mmol) and MeOH (59 mg, 1.82 mmol) in anhydrous CH2Cl2 (20 ml) was treated with 4-dimethylaminopyridine (DMAP, 163 mg, 1.33 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (280 mg, 1.45 mmol). The reaction was stirred for 18 h, diluted with EtOAc (150 ml), washed with water (2×), sat. aq. NaHCO3, and sat. aq. NaCl, dried over Na2SO4 and concentrated in vacuo. Chromatography (flash, SiO2, 0 to 5% MeOH/CH2Cl2) gave 250 mg (67%) of the title compound as a light tan solid.

Provenance & Evidence