Methyl chloroglyoxylate → HCID 58032534, compound

Participants

Reaction Steps

3-(4-{2-tert-Butoxycarbonyl-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-ethyl}-2-fluoro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid methyl ester. A mixture of 3-[3-fluoro-4-(hydroxy-hydroxyimino-methyl)-phenyl]-2-[(4′-methyl-biphenyl-3-carbonyl)-amino]-propionic acid tert-butyl ester (10 g, 0.02 mol) and methyl(chlorocarbonyl)formate (5 g, 0.04 mol), and pyridine (1 mL) in toluene (150 mL) was refluxed overnight. TLC showed the reaction was completed. An aqueous NaHCO3 solution (80 mL) was added to the reaction mixture, the layers were separated, and the aqueous portion was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (2×30 mL), dried over anhydrous sodium sulfate, filtered, concentrated, and purified by chromatography and recrystallization to give the title compound (7 g, 64% yield) as a white solid.

Provenance & Evidence