Synthetic method for N(2)-L-alanyl-L-glutamine dipeptide
A glutamine dipeptide and synthesis method technology, which is applied in the field of amino acid-containing dipeptide synthesis, can solve the problems of many side reactions, high temperature, and high price, and achieve the effects of reasonable production process, low cost, and short synthetic route
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Embodiment 1
[0032] Example 1: Dissolve 20mmol of triphosgene in 10mL of dichloromethane, and add dropwise to the mixed system of 10mmol of N-(O, O-dimethyl)phosphorylalanine, 20mmol of triphenylphosphine, and 20mL of dichloromethane Inside, after reacting at -5°C for 3h, add dropwise to water containing 20mmol glutamine and 20mL, adjust the pH to 10 with potassium hydroxide during the reaction, and the reaction temperature is 0°C, react for 1.5h after dropping, and then use concentrated hydrochloric acid Acidify to pH 2.5, extract N(2)-L-alanyl-L-glutamine dipeptide containing protective groups, and react the intermediate with hydrogen chloride / glacial acetic acid at room temperature for 20 h, add 50 mL of diethyl ether after the reaction, A solid was precipitated, and the solid was recrystallized from isopropanol-water to obtain the product N(2)-L-alanyl-L-glutamine dipeptide. Yield 45%.
Embodiment 2
[0033]Example 2: 10mmol of triphenylphosphine was dissolved in 30mL of tetrahydrofuran, and added dropwise to a mixed system of 10mmol of N-(O, O-diethyl)phosphorylalanine, 15mmol of triphosgene, and 10mL of tetrahydrofuran, at 10 After reacting at ℃ for 1 hour, add it dropwise to water containing 10 mmol glutamine and 20 mL, adjust the pH to 9 with sodium hydroxide during the reaction, and the reaction temperature is 10 ℃, and react for 30 minutes after dropping. Then acidify with dilute nitric acid to pH 1.5, and extract N(2)-L-alanyl-L-glutamine dipeptide containing protective groups. The intermediate is reacted with hydrogen bromide / glacial acetic acid at room temperature for 15h, and the reaction After the completion, 50 mL of ether was added to precipitate a solid, which was recrystallized from methanol-water to obtain the product N(2)-L-alanyl-L-glutamine dipeptide. Yield 40%.
Embodiment 3
[0034] Example 3: Dissolve 15 mmol of triphosgene in 20 mL of toluene, and add dropwise to 10 mmol of N-(O, O-diisopropyl)phosphorylalanine and 15 mmol of triphenylphosphine in 20 mL of toluene at 5°C. After reacting at 5°C for 2 hours, add dropwise to a mixture containing 20mmol glutamine, 20mL water, and 5mL ethanol. During the reaction, potassium carbonate is used to adjust the pH to 9.5, and the reaction temperature is 5°C. After dropping, react for 10min. Then acidify with sulfuric acid to pH 1.0, and extract to obtain N(2)-L-alanyl-L-glutamine dipeptide containing protective groups. The intermediate is reacted with trifluoroacetic acid at room temperature for 10 h, and diethyl ether is added after the reaction 50 mL, a solid was precipitated, and the solid was recrystallized from ethanol-water to obtain the product N(2)-L-alanyl-L-glutamine dipeptide. Yield 50%.
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