Sulfuric Acid → (S)-a-Hydroxy-cyclopropanepropanoic acid

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Reaction Steps

A 1 L, 3-neck flask was equipped with two dropping funnels, one containing 21.3 mL of 2.0 N H2SO4 and the other containing 21.3 mL of 2.0 N NaNO2. A mixture of 5.00 g (38.7 mmol) of 2-(S)-amino-3-cyclopropyl propanoic acid in 28 mL of H2O at 0° C. was treated with a sufficient amount of the acid solution to dissolve the solids. The remaining H2SO4 solution and the NaNO2 solution were added maintaing the internal temperature at less than 5° C. The resulting mixture was stirred cold for 3 h, then warmed to rt and stirred for 20 h. The reaction mixture was saturated with NaCl and extracted with 4×100 mL of EtOAc. The extracts were dried over MgSO4 and concentrated to afford 4.30 g (85%) of the title compound: 1H NMR (300 MHz): δ 0.13-0.18 (m, 2H), 0.48-0.54 (m, 2H), 0.89 (m, 1H), 1.67-1.76 (m, 2H), 4.37 (dd, J=6.4, 4.7 Hz, 1H).

Provenance & Evidence