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Method for preparing N6-benzoyladenosine

A technology for benzoyladenosine and adenosine, which is applied in the field of preparation of N6-benzoyladenosine, can solve problems such as serious environmental pollution and cannot meet environmental protection requirements, achieve environmental friendliness, improve enterprise production efficiency, and reduce costs Effect

Pending Publication Date: 2021-02-09
XINXIANG RUICHENG TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the synthesis process, trimethylchlorosilane is used for protection, and about 0.3 tons of hydrogen chloride gas is generated per ton of product, and a large amount of hexamethyldisilazane waste liquid is generated during deprotection, and about 0.6 tons of organic waste liquid is generated per ton of product , the environmental pollution is serious, and it is far from meeting the current environmental protection requirements.

Method used

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  • Method for preparing N6-benzoyladenosine
  • Method for preparing N6-benzoyladenosine
  • Method for preparing N6-benzoyladenosine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Weigh 100.0g of adenosine and 240.0g of methyl benzoate into a dry four-necked flask, add 800.0g of toluene and 4.0g of p-trifluoroacetic acid, stir, reflux for 2 hours, distill 100ml of solvent, and continue to keep warm 2h;

[0028] (2) Cool the mixture of the above step (1) to 5°C, stir for 0.5h, filter, rinse with 200ml toluene once, and the filter cake is esterified benzoyladenosine;

[0029] (3) Add the filter cake obtained in the above step (2) into a four-necked bottle, add 600g of deionized water and 100g of sodium bicarbonate, heat up to 40°C, stir for 0.5h, filter, and rinse the filter cake with deionized water three times (200ml × 3), dried to obtain N6-benzoyladenosine 93.3g, purity 99.5%, yield 93.3%; the nuclear magnetic spectrum data of product N6-benzoyladenosine are as follows: 1 H NMR (600MHz, DMSO-d 6 )δ11.21 (s, 1H), 8.74 (d, J=23.9Hz, 2H), 8.05 (d, J=7.6Hz, 2H), 7.65 (t, J=7.4Hz, 1H), 7.56 (t, J=7.6Hz, 2H), 6.04(d, J=5.7Hz, 1H), 5.25(d, J=4....

Embodiment 2

[0032] (1) Weigh 100.0g of adenosine and 250.0g of methyl benzoate into a dry four-neck flask, add 1000.0g of toluene and 4.0g of p-trifluoroacetic acid, stir, reflux for 4 hours, distill 200ml of solvent, and continue to keep warm 3h;

[0033] (2) Cool the mixture of the above step (1) to 0° C., stir for 0.5 h, filter, rinse once with 200 ml of toluene, and the filter cake is esterified benzoyladenosine;

[0034] (3) Add the filter cake obtained in the above step (2) into a four-necked bottle, add 600g of deionized water and 100g of sodium bicarbonate, heat up to 30°C, stir for 0.5h, filter, and rinse the filter cake with deionized water three times (200ml×3), dried to obtain N6-benzoyladenosine 94.0g, purity 99.7%, yield 94.0%;

[0035] (4) the filtrate of above-mentioned step (2) is carried out rectifying, isolate the methanol 29.8g wherein, the filtrate distillation of step (3) is separated benzoic acid 114.0g, methyl alcohol and benzoic acid are esterified under sulfuric...

Embodiment 3

[0037] (1) Weigh 20.0g of adenosine and 46.0g of ethyl benzoate into a dry four-neck flask, add 140.0g of benzene and 0.6g of p-toluenesulfonic acid, stir, reflux for 6 hours, distill 20ml of solvent, and continue to keep warm 4h;

[0038] (2) Cool the mixture of the above step (1) to 10° C., stir for 0.5 h, filter, rinse once with 40 ml of benzene, and the filter cake is esterified benzoyladenosine;

[0039] (3) Add the filter cake obtained in the above step (2) into a four-necked bottle, add 120.0g deionized water and 13g sodium carbonate, heat up to 50°C, stir for 0.5h and then filter, and rinse the filter cake with deionized water three times (20ml×3), dried to obtain N6-benzoyladenosine 18.4g, purity 99.6%, yield 92.0%;

[0040] (4) the filtrate of above-mentioned step (2) is carried out rectifying, isolate ethanol 13g wherein, the filtrate distillation of step (3) is separated to go out benzoic acid 34g, and ethanol and benzoic acid are esterified under sulfuric acid ca...

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Abstract

The invention discloses a method for preparing N6-benzoyladenosine. The method comprises the following steps: (1) weighing and adding adenosine and a protectant in a flask, adding a solvent and a catalyst, carrying out stirring refluxing for a period of time, then, distilling off part of the solvent, and continuing to carry out heat preserving treatment, wherein the protectant is an ester formed by benzoic acid and fatty alcohol with carbon atoms in the quantity not greater than 5; (2) cooling the mixture obtained in the step (1), then, continuing to carry out stirring, and carrying out filtering, so as to obtain a filter cake; and (3) adding a weakly alkaline solution into the filter cake obtained in the step (2), carrying out heated-up stirring for a period of time, then, carrying out filtering, and drying a filter cake, thereby obtaining the N6-benzoyladenosine. According to the method for preparing the N6-benzoyladenosine, disclosed by the invention, byproducts of a preparation process are fully utilized, the utilization ratio of atoms is close to 100%, the cyclic utilization of a protectant raw material is achieved, no hazardous and noxious substances is generated, the methodis environmentally friendly, the cost is reduced, and the production efficiency of enterprises is increased.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a preparation method of N6-benzoyladenosine. Background technique [0002] N6-benzoyladenosine, a nucleoside compound, the structural formula is as follows: [0003] [0004] In the prior art, the method for preparing N6-benzoyladenosine usually uses trimethylchlorosilane protection to obtain trimethyl-protected adenosine, then adds benzoyl chloride for benzoylation, and finally under the protection of ammonia water Remove the protection, then concentrate, evaporate the solvent to dryness, and add water to crystallize. During the synthesis process, trimethylchlorosilane is used for protection, and about 0.3 tons of hydrogen chloride gas is generated per ton of product, and a large amount of hexamethyldisilazane waste liquid is generated during deprotection, and about 0.6 tons of organic waste liquid is generated per ton of product , the environmental pollution is serious, a...

Claims

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Application Information

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IPC IPC(8): C07H19/19C07H1/00
CPCC07H19/19C07H1/00
Inventor 范江涛徐俊丽丁国庆白志臣李红涛崔成功
Owner XINXIANG RUICHENG TECH DEV
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