Acetic Acid → HCID 13026601, compound

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).

1. temperaturedropwise under cooling with ice
2. additionAfter the addition
3. extractionextracted with diethyl ether
4. customDiethyl ether was removed by distillation
5. additionto the residue were added 0.5 g of p-toluenesulfonic acid, 300 ml of ethanol, and 100 ml of benzene
6. temperatureby heat-refluxing
7. customwhile removing
8. customby-produced water azeotropically with benzene and ethanol
9. washthe mixture was washed with water
10. dry with materialdried over magnesium sulfate
11. customThe solvent was removed by distillation
12. customto obtain a crude product, which
13. distillationwas then purified by distillation

ORD record

ord-df08b7df469e4654b5e46b14192ba1c0

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093345