2-Chloro-2-hydroxyiminoacetic acid ethyl ester

Chemical Properties

Uses

• in the preparation of (+)-and ()-Δ²-isoxazolines
• in the synthesis of CIP-AS (), a chiral amino acid structurally related to glutamic acid, potential agonist at the ionotropic (±±)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA)-kainate receptors
• to generate ethoxycarbonylformonitrile oxide, in situ by treatment with sodium bicarbonate
• to prepare N-azirdinyloximes which on treatment with scandium triflate (418218) provide dihydro-oxadiazines

Synthesis

459-73-4

14337-43-0

General procedure for the synthesis of ethyl chlorooxime acetate from ethyl 2-aminoacetate: ethyl aminoacetate (5 g, 48.53 mmol) was dissolved in water (5 ml) to form a solution. To this solution, concentrated hydrochloric acid (8 ml) was slowly added at 0°C, followed by a mixture of sodium nitrite (NaNO2, 4.91 g, 145.6 mmol) and water (5 ml). The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under vacuum to give ethyl chloroxime acetate (1.5 g, 20% yield) as a white solid.1H NMR (400 MHz, CDCl3): δ 1.37-1.41 (t, J = 7.2 Hz, 3H); 4.38-4.43 (q, J = 7.2 Hz, 2H). 9.59-9.61 (m, 1H).

References