Acetic Acid → HCID 13026601, compound

Participants

Reaction Steps

In a 300 ml flask were charged 20 g of L-isoleucine (compound (30), R1 =ethyl) and 200 ml of 50% acetic acid, and an aqueous solution of 21 g of sodium nitrite was added thereto dropwise under cooling with ice. After the addition, the mixture was stirred at room temperature for 1 hour and extracted with diethyl ether. Diethyl ether was removed by distillation, and to the residue were added 0.5 g of p-toluenesulfonic acid, 300 ml of ethanol, and 100 ml of benzene, followed by heat-refluxing while removing by-produced water azeotropically with benzene and ethanol. Diethyl ether was added to the reaction mixture, and the mixture was washed with water and dried over magnesium sulfate. The solvent was removed by distillation to obtain a crude product, which was then purified by distillation to obtain 9.5 g (43.7%) of the titled compound (b.p.: 60° C./5 mmHg).

Provenance & Evidence