Methyl chloroformate → (2S,3S)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

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Reaction Steps

A solution of allo-O-methyl-L-threonine (519 mg, 3.90 mmol) in saturated sodium bicarbonate solution (47.6 mL) was treated dropwise with methyl chloroformate (453 μL, 553 mg, 5.85 mmol) followed by stirring at RT for 18 h. The mixture was extracted with ether and the aqueous phase was cooled to 0° C. and acidified to pH 2-3 by addition of concentrated hydrochloric acid solution. The mixture was extracted with ethyl acetate (3×). The combined organic layers were extracted with saturated sodium chloride solution and dried (Na2SO4). Concentration in vacuo afforded the title compound (640 mg, 86%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.48 (d, J=7.8 Hz, 1 H), 4.52 (d, J=4.7 Hz, 1 H), 3.71 (s, 3 H), 3.39 (s, 3 H), 1.25 (t, J=7.6 Hz, 3 H).

Provenance & Evidence