Sodium Hydroxide → 2-(((Benzyloxy)carbonyl)amino)malonic acid

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Reaction Steps

Compound 2 (3.49 mmol, 1.08 g) was dissolved in 3 mL 95% ethanol and treated with 3.49 mL 2N NaOH. The clear, colorless solution was left at room temperature for 19 hours until no starting material could be detected by tlc on silica gel (benzene:ethyl acetate, 4:1). Ethanol was evaporated under reduced pressure at room temperature. The aqueous solution was washed once with ether and then acidified with concentrated HCl to pH 2.5. The milky solution was extracted with ethyl acetate (3x). The pooled extract was washed with brine, dried over anhydrous Na2SO4 and evaporated to dryness. The product was crystallized from ether to yield 0.852 g of compound 3; mp 144°-145° C.; homogeneous by the tlc on silic gel (CHCl3 :methanol:acetate acid, 5:13:1); 250 MHz nmr (acetone-d6, ppm) 5.00 (1H, d, J=8 Hz, α--H), 5.10 (2H, s, ArCH2 --), 6.84 (1H, d, J=8 Hz, amide H), 7.36 (5H, m, ArH5). In a 60 MHz spectrum run in low water content acetone, a 9.7 ppm (2H, broad s, exchangeable with D2O) was also observed.

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