Sodium Chloride → Ethyl 3-nitriloalaninate

HRID 408827Notes

Reaction equation

HRID 408827 reaction equation
[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]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 6399078Ethyl 2-cyano-2-(hydroxyimino)acetate

Product 1

HCID 931182Ethyl 3-nitriloalaninate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

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).

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with CH2Cl2 (6×150 mL)
  3. dry with materialThe combined CH2Cl2 extracts are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-755a9a0554e64c618219d9412cf59cfe
Source dataset
uspto-grants-2014_06
Patent number
US08759361B2

Reaction notes

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