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Preparation method of N-isobutyrylguanosine

A technology of isobutyryl guanosine and isobutyryl chloride is applied in the field of preparation of N-isobutyryl guanosine, which can solve the problem of low yield, lower product quality, and the number of reactions between isobutyryl chloride and methyl deoxyguanosine Less problems, high yield and high quality

Inactive Publication Date: 2021-12-21
马鞍山致研生物医药科技有限公司
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  • Claims
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AI Technical Summary

Problems solved by technology

[0003] The prior art has the following deficiencies: N-isobutyryl guanosine is mainly prepared by synthesizing isobutyryl chloride and methyl deoxyguanosine, but when isobutyryl chloride is synthesized, there is no ratio optimization process for the synthetic material of isobutyryl chloride , and the number of reactions between isobutyryl chloride and methyl deoxyguanosine is small, which leads to the bottom of the overall yield of the product and reduces the quality of the product

Method used

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  • Preparation method of N-isobutyrylguanosine
  • Preparation method of N-isobutyrylguanosine
  • Preparation method of N-isobutyrylguanosine

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Experimental program
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Embodiment 1

[0032] see figure 2 Shown, S1: Synthesis of isobutyryl chloride

[0033] In a 1000mL reactor with stirrer, constant pressure titration funnel, spherical condenser and thermometer, add 1084g (9.1mol) thionyl chloride, then add 704g (8mol) isobutyric acid in the constant pressure titration funnel , open the water supply valve of the spherical condensation, and start to stir continuously, then add isobutyric acid dropwise under stirring, thionyl chloride and isobutyric acid react at a certain temperature, and the tail gas generated by the reaction is condensed and discharged HCl, SO2, isobutyric acid After the addition of butyric acid is completed, continue to stir and raise the temperature to 80°C, ripen for 40 minutes, and rectify the reaction liquid on the tower. The fraction at ℃ is the synthesized isobutyryl chloride;

[0034] The molecular formula of synthetic isobutyryl chloride is The molecular weight is 106.551, the density is 1.0±0.1g / cm3, the boiling point is 90.9...

Embodiment 2

[0041] S2: Guanosine synthesis

[0042] Put the guanine and the ribose ring into the mixer and mix them, and then connect the guanine and the ribose ring through the β-N9-glycosidic bond to obtain guanosine;

[0043]Guanine is prepared by the following steps:

[0044] (1) In a 100ml double-necked round bottom flask with a distillation device, add 6g of potassium hydroxide, dissolve it with 10ml of water, keep the temperature of the water bath at 60-70°C, and add 35ml of methyl cellosolve under stirring to make it Mix well, then add dropwise 35ml of ether solution containing 5.25g of N-methyl-N-nitroso-p-toluenesulfonamide to this solution, keep the solution under reflux, cool the receiver with an ice bath, and the distillate is diazomethane ether solution;

[0045] (2) Dissolve 0.25g of 2'-deoxynucleoside in 75ml of methanol, keep at 0°C, then add diazomethane ether solution, continue to maintain at 0°C, react for 2h, filter out the white precipitate, wash twice with a small...

Embodiment 3

[0049] see figure 1 Shown, S3: N-isobutyrylguanosine synthesis

[0050] S3.1: Add the isobutyryl chloride liquid obtained in step S1 and the methyl deoxyguanosine obtained in step S2 to the reactor for one reaction, the reaction time is 24 hours, the reaction temperature is 40°C, and the internal temperature of the reactor after the reaction down to 0°C;

[0051] S3.2: Then add methanol to the reactor and carry out a secondary reaction. The secondary reaction time is 4 hours, and the reaction temperature is 60°C. After the reaction, the mixed solution is concentrated in a distillation equipment, and the temperature of the distillation equipment is 120°C;

[0052] S3.3: Finally, put the concentrated solution into the reactor, then add the mixed solution of n-ethane and diethyl ether to carry out three reactions, the volume ratio of n-ethane and diethyl ether is 1:1, the three-time reaction time is 12h, and the reaction temperature is 30°C , standing for 2 hours after the reac...

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Abstract

The invention provides a preparation method of N-isobutyrylguanosine. The method comprises the following steps: S1: synthesis of isobutyryl chloride: adding thionyl chloride into a reactor, then adding isobutyric acid into a constant-pressure titration funnel according to a ratio of thionyl chloride to isobutyric acid of 1.2: 1, and performing stirring, S2: synthesis of guanosine; and S3: synthesis of the N-isobutyrylguanosine. When the isobutyryl chloride is synthesized, the ratio of the thionyl chloride to the isobutyric acid is optimized, when the ratio of the thionyl chloride to the isobutyric acid is 1.2: 1, the yield of the synthesized isobutyryl chloride is 75.7%, and when the isobutyryl chloride and methyl deoxyguanosine are synthesized, the N-isobutyrylguanosine is prepared through three times of reactions. According to the preparation method, the synthesis proportion of the isobutyryl chloride is optimized, the isobutyryl chloride and the methyl deoxyguanosine react for multiple times to prepare the N-isobutyrylguanosine, the product quality is high, and the yield is high.

Description

technical field [0001] The invention relates to the technical field of N-isobutyryl guanosine preparation, in particular to a preparation method of N-isobutyryl guanosine. Background technique [0002] The appearance of N-isobutyryl guanosine is white crystal. N-isobutyryl guanosine is mainly used as a pharmaceutical intermediate reagent. Store in light, keep away from heat sources, stable under normal temperature and pressure, keep away from oxidants. [0003] The prior art has the following disadvantages: N-isobutyryl guanosine is mainly prepared by synthesizing isobutyryl chloride and methyl deoxyguanosine, but when isobutyryl chloride is synthesized, there is no ratio optimization process for the synthetic material of isobutyryl chloride , and the number of times of reaction between isobutyryl chloride and methyl deoxyguanosine is small, thereby causing the bottom of the overall yield of the product and reducing the quality of the product. Contents of the invention ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H1/00C07H19/167
CPCC07H1/00C07H19/167
Inventor 张业林
Owner 马鞍山致研生物医药科技有限公司
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