Synthesis of tenuazonic acid and iso-tenuazonic acid

A technology of alternaria tenoic acid and amino acid, which is applied in the direction of organic chemistry, can solve the problems of unsuitability for industrial production, poor safety, cumbersome purification, etc., and achieve simple production equipment requirements, low production cost, and easy operation Effect

Inactive Publication Date: 2006-08-16
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method requires cumbersome purification after amidation, and gaseous diazomethane is used for esterification,

Method used

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  • Synthesis of tenuazonic acid and iso-tenuazonic acid
  • Synthesis of tenuazonic acid and iso-tenuazonic acid
  • Synthesis of tenuazonic acid and iso-tenuazonic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 30mL of absolute ethanol to a dried 100mL three-neck flask equipped with a thermometer and a stirrer, add 0.8g (0.022mol) of dry HCl gas, add 2.63g (0.02mol) of isoleucine, heat, reflux, Stirring, reaction 3h, left overnight. Add 1.5g (0.022mol) of sodium ethoxide (newly made), stir and react for 0.5h. 1.85 g (0.022 mol) of diketene was added dropwise, and the drop was completed within 1 h. During the dropwise addition, the temperature was controlled below 10° C., and then stirred and reacted at room temperature for 4 h. Add 20 mL of benzene, 1.56 g (0.023 mol) of sodium ethoxide (newly produced), reflux, stir, react for 3 hours, let stand overnight, remove the solvent under reduced pressure, dissolve with 30 mL of water, extract with ethyl acetate 2×10 mL, and use 10 % of dilute sulfuric acid to neutralize, and then extracted with ethyl acetate 3×10mL, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to obtain 3.6g of yellow viscous liquid...

Embodiment 2

[0029] Add 30mL of absolute ethanol to a dried 100mL three-necked flask equipped with a thermometer and a stirrer, add 0.8g (0.022mol) of dry HCl gas, add 2.63g (0.02mol) of leucine, heat, reflux, and stir , reacted for 3h and left overnight. Add 1.5g (0.022mol) of sodium ethoxide (newly made), stir and react for 0.5h. 1.85 g (0.022 mol) of diketene was added dropwise, and the drop was completed within 1 h. During the dropwise addition, the temperature was controlled below 10° C., and then stirred and reacted at room temperature for 4 h. Add 20 mL of benzene, 1.56 g (0.023 mol) of sodium ethoxide (newly produced), reflux, stir, react for 3 hours, let stand overnight, remove the solvent under reduced pressure, dissolve with 30 mL of water, extract with ethyl acetate 2×10 mL, and use 10 % of dilute sulfuric acid to neutralize, then extracted with ethyl acetate 3×10mL, dried over anhydrous sodium sulfate, distilled off 20mL of solvent, cooled and crystallized to obtain 3.2g of l...

Embodiment 3

[0031] Add 30L of absolute ethanol to the dried 100L reaction kettle equipped with a thermometer and agitator, feed 0.8kg (22mol) of dry HCl gas, add 2.63kg (20mol) of isoleucine, heat, reflux, and stir. Reaction 3h, left overnight. Add 1.5kg (22mol) of sodium ethylate (newly made), stir, and react for 0.5h. 1.85 kg (22 mol) of diketene was added dropwise, and the drop was completed within 1 hour. During the dropwise addition, the temperature was controlled below 10° C., and then stirred and reacted at room temperature for 4 hours. Add 20L of benzene, 1.56kg (23mol) of sodium ethoxide (newly made), reflux, stir, react for 3h, stand overnight, remove the solvent under reduced pressure, dissolve with 30L of water, extract with ethyl acetate 2×10L, and use 10% Neutralize with dilute sulfuric acid, then extract with ethyl acetate 3×10L, dry over anhydrous sodium sulfate, evaporate the solvent to obtain 3.56kg of yellow viscous liquid. After testing, the content of alternarinic a...

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Abstract

Synthesis of tenuazonic acid and isotenuazonic acid is carried out by taking amino acid as initial material, esterifying by alcohol, neutralizing by sodium alcoholate, acidylating by diketene, cyclizing and acidifying under the existence of sodium alcoholate to obtain final product. It is simple, safe and cheap, has more yield and better quality.

Description

1. Technical field [0001] The invention relates to a production technology of alternarione acid and alternarione acid, belongs to the technical field of compound synthesis, and is specially used for synthesizing alternarione acid and alternarione acid . 2. Background technology [0002] Rosett T. et al. (ibid., 1957, 67: 390) and Stickings C.E. (Biochem. J., 1959, 72: 332) successively discovered that tenuazonic acid (Tenuazonic acid) has antitumor activity, and then Miller F.A. , etc. (Nature, 1963, 200: 1338) found that alternarinic acid also had weak antiviral activity, and Qiang Sheng was equal to 2005 and found that alternarinic acid and isoalternarinic acid ( Iso-tenuazonic acid) has broad-spectrum, rapid and efficient herbicidal activity (CN 1644046A, 2005-07-27). Alternaria tenoic acid and alternaria isotenarione acid are toxins secreted by Alternaria, which have a wide range of biological activities, and the research on their synthesis methods has very important t...

Claims

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Application Information

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IPC IPC(8): C07D207/38
Inventor 杨春龙强胜黄林张培朱兆勇
Owner NANJING AGRICULTURAL UNIVERSITY
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