Potassium Carbonate → Carbamic acid, N-[(1S)-1-[[(3-hydroxy-2,2-dimethylpropyl)amino]carbonyl]-2-methylpropyl]-, 1,1-dimethylethyl ester

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Reaction Steps

A solution of commercial 3-amino-2,2-dimethyl-1-propanol (1.7 g, 16.5 mmol), N-[(1,1-dimethylethoxy)carbonyl]-D-Valine, 2,5-dioxo-1-pyrrolidinyl ester (Giuntini F. et al., J. Med. Chem. (2009), 52(13), 4026-4037, incorporated herein by reference) (4.7 g, 15.0 mmol) and 1M aqueous potassium carbonate (10 mL, 10.0 mmol) in acetonitrile (30 mL) was stirred at room temperature for 2 h. The mixture was concentrated to about one third of its volume, diluted with 1M hydrochloric acid and extracted three times with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, filtered and the filtrate evaporated to a residue. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (50:50) to isolate 4 g (88% yield) of tert-butyl N-[(1S)-1-[(3-hydroxy-2,2-dimethyl-propyl)carbamoyl]-2-methyl-propyl]carbamate.

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