Imidazole → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

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Reaction Steps

To a solution of 44.2 g (0.65 mole) of imidazole in methylene chloride (300 ml) is added with stirring 19.4 ml (0.13 mole) of phenyldichlorophosphate. The mixture is stirred at room temperature for 0.5 hour, and then cooled to 0° C. A solution of 34.5 g (0.13 mole) of N-t-butoxycarbonyl-L-phenylalanine in 10 methylene chloride (120 ml) is added, and the mixture is stirred at 0° C. for 1 hr. N,O-dimethylhydroxylamine hydrochloride (15.2 g, 0,156 mole) is then added in small portions. The resulting mixture is stirred at 0° C. for 5 hours and at room temperature for 16 hours. The final suspension is diluted with 400 ml of methylene chloride, washed with 1N hydrochloric acid (2×200 ml), water (200 ml), saturated potassium carbonate solution (200 ml), and brine (200 ml), and dried over anhydrous magnesium sulfate. Removal of solvents gives 40.2 g of the title compound as a pale yellow oil, [α]D26 +22°±1 (c, 1.052, CHCl3).

Provenance & Evidence