Synthetic method of kainic acid
A synthetic method and technology of kainic acid, which is applied in the field of synthesis of natural product kainic acid, achieves the effects of reducing synthesis cost, simple operation process and low price
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0020] 1. Add 1.37 g (59.6 mmol) of metallic sodium into 120 mL of dry absolute ethanol, and stir at room temperature for 2 hours to completely dissolve the metallic sodium to obtain a 0.5 mol / L sodium ethoxide solution. Add 5.6 g (23.8 mmol) of (S)-5-oxo-tetrahydrofuran-3-carbamic acid benzyl ester to the flask, stir at room temperature for 3 hours, add 60 mL of 1 mol / L hydrochloric acid aqueous solution to quench the reaction, and extract with 100 mL of ethyl acetate 3 times, the organic phases were combined, dried with anhydrous sodium sulfate, filtered, concentrated by a rotary evaporator, and purified by column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate with a volume ratio of 3:1), 4.0 g of white solid compound 1 was obtained with a yield of 97%.
[0021] 2. Add 277 mg (6.93 mmol) of sodium hydride and 200 mL of dry N,N-dimethylformamide into the reaction flask, and under the protection of argon, cool to -40°C; dissolve 1.0 g (5.77 mmol)...
Embodiment 2
[0027] In step 2 of Example 1, 15 mg (0.3753 mmol) of sodium hydride and 2 mL of dry N,N-dimethylformamide were added to the reaction flask, cooled to -40°C under argon protection; 50 mg ( 0.2887 mmol) Compound 1 was dissolved in 1 mL of dry N,N-dimethylformamide, slowly injected into the reaction flask with a syringe, and stirred at -40°C for 30 minutes; 58.2 mg (0.3176 mmol) of (E) -4-Bromo-1-chloro-2-methyl-2-butene was dissolved in 1 mL of dry N,N-dimethylformamide, slowly injected into the reaction flask with a syringe, and continued at -40°C Stir for 30 minutes; the reaction is warmed to room temperature, 480 mg (2.887 mmol) of dry potassium iodide and 0.3 mL (0.433 mmol) of lithium bis-trimethylsilyl amide are added, stirred for 3 hours, and quenched with saturated aqueous ammonium chloride after the reaction is complete The reaction was extracted three times with 10 mL of ethyl acetate, and the organic phases were combined, washed with saturated sodium chloride water (...
Embodiment 3
[0029] In step 3 of Example 1, 1.52 g (4.04 mmol) of pyridinium dichromate used was replaced with 1.33 g (3.14 mmol) of Dess-Martin oxidizing agent, and other steps in this step were the same as in Example 1, to obtain 308 mg of colorless Transparent liquid compound 3, the yield was 85%. The other steps were the same as in Example 1 to obtain kainic acid with a total yield of 16.2%.
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More