Sodium Chloride → Ethyl 3-nitriloalaninate
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[C:1]([C:3](=[N:9]O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[Na+].[Cl-]>O>[N:2]#[C:1][C@@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH2:9][C:1]([C:3](=[N:9]O)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].[Na+].[Cl-]>O>[N:2]#[C:1][C@@H:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH2:9]A mixture of ethyl cyanoglyoxylate-2-oxime (50 g, 352 mmol) in 440 mL of water is cautiously treated with 340 mL of saturated aqueous NaHCO3, followed by portionwise addition of sodium hydrosulfite (165 g, 950 mmol). The reaction is then heated to an internal temperature of 35° C. for 35 min. After cooling to RT, the reaction is saturated with NaCl (approx. 250 g) and extracted with CH2Cl2 (6×150 mL). The combined CH2Cl2 extracts are dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound as a brown oil. 1H NMR (400 MHz, CDCl3) δ 4.43 (1H, s), 4.34 (2H, q, J 7.2), 2.30 (2H, bs), 1.35 (3H, t, J 7.2).
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