Caffeic acid-lysine and derivatives, preparation method and application thereof
A technology of lysine derivatives and caffeic acid, which is applied in the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of high toxicity, non-specific activity, etc. The raw materials are easy to obtain and the effect of preventing and treating diabetes
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example 1
[0046] Example 1 Synthesis of caffeic acid-lysine (abbreviated as C1, shown in formula II-1)
[0047]
[0048] 1) Weigh 90mg (0.5mmol) of caffeic acid and add it to a 10mL round bottom flask, add 4mL DCM (dichloromethane) dropwise to the round bottom flask to dissolve the caffeic acid;
[0049] 2) Add 280 μL (about 2 mmol) of triethylamine to the round bottom flask, stir and cool to 0°C in an ice-water bath;
[0050] 3) Add 190 mg (1 mmol) of EDCI (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) and DMAP (4 -Dimethylaminopyridine) 122mg (1mmol), add 91mg (0.5mmol) of L-lysine hydrochloride to the round bottom flask after 30min, the temperature rises to room temperature (25°C), and continue to react under stirring conditions 24 hours;
[0051] 4) After the reaction was completed, the solvent was vacuum-dried (rotary evaporation, -0.08MPa, 45°C), and 8 mL of ethyl acetate was added to shake well, and filtered with suction. Wash with saturated brine, dry over an...
example 2
[0052] Example 2 Synthesis of caffeic acid-lysine methyl ester (abbreviated as C2, shown in formula II-2)
[0053]
[0054] 1) Weigh 90mg (0.5mmol) of caffeic acid and add it to a 10mL round bottom flask, add 5mL of chloroform dropwise to the round bottom flask to dissolve the caffeic acid;
[0055] 2) Add 140 μL (about 1 mmol) of diisopropylethylamine to the round-bottomed flask, stir and cool to 0°C under an ice-water bath;
[0056] 3) Add 154mg (0.75mmol) of DCC (dicyclohexylcarbodiimide) and 91.5mg (0.75mmol) of DMAP (4-dimethylaminopyridine) to the round bottom flask under ice-water bath and stirring conditions, 10min Then, 196 mg (1 mmol) of L-lysine methyl ester hydrochloride was added to the round bottom flask, the temperature was raised to 25° C., and the reaction was continued for 24 hours under stirring;
[0057] 4) After the reaction was completed, the solvent was vacuum-dried (rotary evaporation, -0.08MPa, 45°C), and 10 mL of ethyl acetate was added to shake w...
example 3
[0058] Example 3 Synthesis of ferulic acid-lysine isopropyl ester (abbreviated as C3, shown in formula III)
[0059]
[0060] 1) Weigh 97mg (0.5mmol) of ferulic acid and add it to a 10mL round bottom flask, add 3mL THF (tetrahydrofuran) dropwise to the round bottom flask to dissolve the ferulic acid;
[0061] 2) Add 210 μL (about 1.5 mmol) of diisopropylamine to the round-bottomed flask, stir and cool to 0°C in an ice-water bath;
[0062] 3) Add 202 mg (2 mmol) of NMM (N-methylmorpholine) and 269 mg (2 mmol) of IBCF (isobutyl chloroformate) to the round-bottomed flask under ice-water bath and stirring conditions, and pour into the round-bottomed flask after 20 minutes. Then add 376 mg (2 mmol) of L-lysine isopropyl ester hydrochloride, the temperature rises to 25°C, and the reaction is continued for 18 hours under stirring;
[0063] 4) After the reaction was completed, the solvent was vacuum-dried (rotary evaporation, -0.08MPa, 45°C), and 15 mL of ethyl acetate was added t...
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