Potassium Carbonate → methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate

Participants

Reaction Steps

To a stirred solution of tert-butyl (2-methyl-3-oxopropyl)carbamate (2.0 g, 8.9 mmol) in ethanol was added D-Alanine methyl ester hydrochloride (1.25 g, 8.9 mmol), followed by potassium carbonate (0.62 g, 4.5 mmol). The resulting mixture was stirred at room temperature for 3 hr. Sodium cyanoborohydride (0.63 g, 10 mmol) was added in one portion. The reaction mixture was stirred at room temperature overnight. The solvent was removed on a rotavap, and the residue was taken up into water and extracted with ethyl acetate (3×). The combined organic extract was washed with brine, dried over sodium sulfate and evaporated to yield methyl N-{3-[(tert-butoxycarbonyl)amino]-2-methylpropyl}-D-alaninate as colorless viscous oil, which was used without further purification. MS (M+1−Boc): 175.3

Provenance & Evidence