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Method for synthesizing glucurolactone

A synthetic method, glucuronolactone technology, applied in chemical instruments and methods, sugar compounds with non-glycosyl groups, drug combinations, etc., can solve the problems of many by-products, environmental pollution, waste of resources, etc., and achieve easy separation and purification , reduce the three wastes pollution, reduce the effect of nitrogen oxides

Active Publication Date: 2009-08-12
JIANGSU TASLY DIYI PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The oxidation selectivity of this process is poor, and the degree of oxidation cannot be effectively controlled; there are many by-products, which lead to difficulty in separating the main product, and the product yield is low, generally below 12%, resulting in a great waste of resources; Nitrogen oxides and crystallization mother liquor, etc. lead to serious environmental pollution, so it is necessary to explore new synthetic routes

Method used

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  • Method for synthesizing glucurolactone

Examples

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Effect test

Embodiment 1

[0035] In 100ml of 0.5M sodium hydroxide, add 10g of methyl glucoside and stir to dissolve at 15°C; then add 1.5g of sodium bromide and 0.2g of catalyst TEMPO, stir to dissolve, cool to 5-10°C and add 120g of 12.5% ​​sodium hypochlorite solution dropwise After the dropwise addition, keep the temperature for reaction for 6 hours, add 5 g of sodium thiosulfate to terminate the oxidation reaction, cool and filter to obtain the oxidation solution. In the oxidation solution, adjust the pH value to 1-2 with dilute hydrochloric acid. Heated to 85°C; hydrolyzed for 5 hours, and the liquid product was treated with a strong acidic cation exchange resin to remove metal ions to obtain a glucuronic acid solution; then concentrated to 30% of the volume, added 6 g of glacial acetic acid, heated to 50°C, and reacted for 8 hours; The reaction mixture was concentrated (40Be), cooled to 5°C, crystallized, filtered and dried to obtain 3.8 g of glucuronolactone. The yield was 41.9%; the content w...

Embodiment 2

[0037] In 100ml of 1M sodium bicarbonate, add 10g of methyl glucoside at 15°C and stir to dissolve; then add 1.5g of sodium bromide and 0.23g of catalyst 4-OH-TEMPO and stir to dissolve, cool to 15-20°C and add 120g of 12. 5% sodium hypochlorite solution, after the dropwise addition, keep the reaction at 30-40°C for 1 hour, add 5 g of sodium thiosulfate under cooling to terminate the oxidation reaction, cool and filter to obtain the oxidation solution. In the oxidation solution, adjust the pH value to 1-2 with dilute nitric acid. Heated to 90°C; hydrolyzed for 5 hours, and the liquid product was treated with a strong acidic cation exchange resin to remove metal ions to obtain a glucuronic acid solution; then concentrated to 30% of the volume, added 6 g of glacial acetic acid, heated to 55°C, and reacted for 6 hours; The reaction mixture was concentrated (39Be), cooled to 5°C, crystallized, filtered and dried to obtain 3.65 g of glucuronolactone. The yield was 40.2%; the conte...

Embodiment 3

[0039] In 100ml of 0.5M sodium bicarbonate, add 10g of methyl glucoside and stir to dissolve at room temperature at 16°C; add 50ml of dichloromethane, then add 1.5g of sodium bromide and 0.2g of catalyst TEMPO, stir to dissolve, drop at 30-40°C Add 100g30%H 2 o 2 After the solution was added dropwise, the reaction was kept for 8 hours, and 15 g of sodium thiosulfate was added to terminate the oxidation reaction, cooled and filtered; the organic layer was separated to obtain an oxidized solution. In the oxidation solution, adjust the pH value to 1-2 with dilute hydrochloric acid. Heat to 90°C; hydrolyze for 4 hours, and the liquid product is treated with a strong acidic cation exchange resin to remove metal ions to obtain a glucuronic acid solution; then concentrate to 30% of the volume, add 6 g of glacial acetic acid, heat up to 40°C, and react for 16 hours; The reaction mixture was then concentrated with 41Be, cooled to 0°C, crystallized, filtered and dried to obtain 3.9 g ...

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Abstract

The invention discloses a synthetic method for glucurolactone, which comprises the following steps: (1) in the alkalescence condition, methyl glycoside, metal halide, and nitroxyl free radical compound are added, stirred and dissolved; oxidant solution is added and reacts for 0.5-8 hours to obtain an oxidizing solution; (2) the obtained oxidizing solution is hydrolyzed for 2-10 hours in the temperature of 50-100 DEG C in the alkalescence condition in the temperature of 50 to 100 DEG C; (3) glacial acetic acid or acetic anhydride are added into hydrolysate and react for 6-16 hours in the temperature of 40-60 DEG C; (4) the reaction solution obtained in the step (3) is concentrated into 35-45 Be, then is cooled to be minus 5 to 5 DEG C, filtered and dried. The synthetic method has good selectivity, few byproducts, easy monitoring reaction process, simplified operation, low cost, and high yield coefficient. The obtained product has good quality; and the production process has little pollution and is environmental friendly.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a synthesis method of glucuronolactone. Background technique [0002] Glucuronolactone, also known as Gantyle and Glucuronolactone, has definite curative effect in liver protection and liver protection, with mild side effects. The mechanism of protecting the liver is: when the liver cells are damaged, the detoxification function of the liver declines, and glucuronolactone enters the body under the action of enzymes and becomes glucuronic acid, which can be combined with toxic substances containing hydroxyl or carboxyl groups to form non-toxic substances. Toxic or low toxic glucuronides are excreted in urine. In addition, this product can reduce the activity of hepatic amylase, prevent the decomposition of glycogen, increase the content of hepatic glycogen, and reduce the accumulation of fat in the liver; moreover, glucuronolactone is also a constituent of human connective tissue an...

Claims

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Application Information

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IPC IPC(8): C07H7/033C07D493/04A61P1/16
Inventor 黄春森杨国军朱占元
Owner JIANGSU TASLY DIYI PHARMA CO LTD
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