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Method for preparing diacetylacyclovir with 7-bit diacetylacyclovir

A technology of diacetyl acyclovir and butanediol diethyl ester, applied in the field of pharmaceutical chemical intermediate synthesis, can solve the problems of only 91% product purity, unfavorable industrial production, low product purity, etc., saving manpower and material resources, The effect of improving resource utilization and high purity

Active Publication Date: 2014-09-03
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The conversion rate of this process reaches 80%, but the product purity is only 91%, and the purification is difficult, which is not conducive to industrial production
The ubiquitous problems of the above traditional synthetic methods are: low product purity and difficult separation. Therefore, it is extremely urgent to find a diacetyl acyclovir isomer recovery method with high conversion yield, easy separation of products and high purity.

Method used

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  • Method for preparing diacetylacyclovir with 7-bit diacetylacyclovir

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preparation example Construction

[0031] Preparation of catalyst organic ammonium trifluoromethanesulfonate: as shown in Table 1 below, add 20 mmol of organic amines into a 100 mL single-necked bottle equipped with a constant pressure dropping funnel and magnetic stirring, and dissolve with 50 mL of toluene. Under ice bath, 3.0 g (20 mmol) of trifluoromethanesulfonic acid was added dropwise. After the dropwise addition, the mixture was stirred and reacted under ice bath for 0.5 h, and a light blue solid was precipitated. After suction filtration, the filter cake was vacuum-dried at 60°C to obtain the corresponding organic ammonium trifluoromethanesulfonate catalyst.

[0032] Table 1

[0033] catalyst

[0034] Diphenylamine triflate

Embodiment 1

[0036] Add 15.4g (0.05mol) 7-DACV, 0.96g (3.0mmol) diphenylamine triflate, 1.76g (0.01mol) 2-oxa-1 into a 500mL three-necked flask equipped with mechanical stirring and a thermometer , 4-butanediol diethyl ester, 10.2g (0.10mol) acetic anhydride, , 100mL chloroform, start heating up, react at 70°C for 25h, after the reaction is over, cool, filter, wash the filter cake with water until the filtrate becomes clear, Then the filter cake was dried to obtain 12.4 g of diacetyl acyclovir, the yield was 80.0%, and the HPLC detection content was 97.6%.

Embodiment 2

[0038]Add 15.4g (0.05mol) 7-DACV, 1.82g (6.0mmol) diphenylamine trifluoromethanesulfonate, 17.6g (0.1mol) 2-oxa-1 into a 500mL three-necked flask equipped with mechanical stirring and a thermometer , 4-butanediol diethyl ester, 20.4g (0.20mol) acetic anhydride, 150mL xylene, start heating up, react at 90°C for 20h, after the reaction is over, cool, filter, wash the filter cake with water until the filtrate becomes clear, Then the filter cake was dried to obtain 13.0 g of diacetyl acyclovir, the yield was 84.8%, and the HPLC detection content was 95.8%.

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Abstract

The invention discloses a method for preparing diacetylacyclovir with 7-bit diacetylacyclovir. The 7-bit diacetylacyclovir, 2-oxa-1, 4-butanediol diethyl ester and acetic anhydride react in organic solvents at the controlled temperature of 30-150 DEG C for 1-30h under the action of trifluoromethanesulfonic acid ammonium salt catalysts, and the target product of diacetylacyclovir is obtained by means of separation and purification after reaction. The method is moderate in reaction condition, short in cycle and simple and convenient in operation, the reaction process is easy to control, the 7-bit diacetylacyclovir can be converted into the diacetylacyclovir, the conversion rate is high, and the product with high purity can be obtained by means of simple operation after conversion. By the aid of the conversion process, the cost for treating waste gas, waste water and waste residues is reduced, resource utilization rate is increased, and the method is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to the field of synthesis of pharmaceutical and chemical intermediates, in particular to a method for preparing the 9-position diacetyl acyclovir, a key intermediate of acyclovir and valacyclovir, using the 7-position diacetyl acyclovir as a raw material. (2) Technical background [0002] Nucleoside antiviral drugs, because of their similar chemical structure to nucleotides, can selectively enter viral cells and participate in the replication process of viral DNA and RNA, thereby blocking viral replication and achieving antiviral effects. Clinically, the Drugs are mainly used against herpes virus, varicella zoster virus, etc. At present, such drugs mainly include acyclovir, valacyclovir, famciclovir, etc., and these drugs have become remarkable active varieties in the antiviral drug market at home and abroad, with a large market demand and an increasing trend year by year . [0003] The 9-position diacetyl acyclovir (DACV) i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/18
Inventor 李坚军蒲通鞠金军苏为科王乃星
Owner ZHEJIANG UNIV OF TECH
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