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A method for synthesizing cyclic adenosine monophosphate

A technology for cyclic adenosine monophosphate and adenosine acid, which is applied in the field of synthesizing cyclic adenosine monophosphate, can solve the problems of solvent waste and unsuitability for industrial production, and achieve the effects of shortened steps, novel design routes, and simple operation processes

Active Publication Date: 2021-08-27
TUOXIN GROUP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are easy to obtain, and the reaction conditions are mild and moderate, but the amount of solvent used is hundreds of times that of the raw materials, and the solvent waste is serious, which is not suitable for industrial production.

Method used

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  • A method for synthesizing cyclic adenosine monophosphate
  • A method for synthesizing cyclic adenosine monophosphate
  • A method for synthesizing cyclic adenosine monophosphate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] In the first step, add 173.5g (0.5mol) of adenosine acid, 108g (1.05mol) of acetic anhydride, 111g (1.1mol) of triethylamine, and 500mL of dichloroethane into the reactor, and heat up to 70°C to 80°C for reaction After 4-6 hours, the liquid phase was tracked until the raw materials disappeared, and the unreacted adenylic acid was removed by cooling and filtering, and the filtrate was concentrated to obtain the crude acetyl-protected cyclic adenosine monophosphate, whose molecular weight was confirmed by LC-MS to be consistent with the described intermediate.

[0027] In the second step, in the reaction kettle, add crude acetyl-protected cyclic adenosine monophosphate, 100mL of water, dropwise add 250mL of 20% sodium hydroxide aqueous solution, control the temperature at 20-25 degrees, keep the reaction for 5 hours after the addition is completed, and follow the reaction in the liquid phase to The intermediate disappeared, the reaction liquid was adjusted to p...

Embodiment 2

[0029]

[0030] In the first step, add 173.5g (0.5mol) of adenosine acid, 108g (1.05mol) of acetic anhydride, 111g (1.1mol) of triethylamine, and 500mL of chloroform into the reactor, and heat up to 70°C to 80°C for 4-6h , the liquid phase was tracked until the raw materials disappeared, the temperature was lowered and filtered to remove unreacted adenosine, and the filtrate was concentrated to obtain the crude acetyl-protected cyclic adenosine monophosphate.

[0031] In the second step, in the reaction kettle, add crude acetyl-protected cyclic adenosine monophosphate, 100mL of water, dropwise add 250mL of 20% sodium hydroxide aqueous solution, control the temperature at 20-25 degrees, keep the reaction for 5 hours after the addition is completed, and follow the reaction in the liquid phase to The intermediate disappeared, the reaction solution was adjusted to pH=7, concentrated under reduced pressure until the remaining 80mL of the reaction solution was adjusted to pH=4 to ...

Embodiment 3

[0033]

[0034] In the first step, add 173.5g (0.5mol) of adenosine acid, 108g (1.05mol) of acetic anhydride, 111g (1.1mol) of triethylamine, and 500mL of acetonitrile into the reactor, and heat up to 70°C to 80°C for 4-6h , the liquid phase was tracked until the raw materials disappeared, the temperature was lowered and filtered to remove unreacted adenosine, and the filtrate was concentrated to obtain the crude acetyl-protected cyclic adenosine monophosphate.

[0035] In the second step, in the reaction kettle, add crude acetyl-protected cyclic adenosine monophosphate, 100mL of water, dropwise add 250mL of 20% sodium hydroxide aqueous solution, control the temperature at 20-25 degrees, keep the reaction for 5 hours after the addition is completed, and follow the reaction in the liquid phase to The intermediate disappears, the reaction solution is adjusted to pH=7, concentrated under reduced pressure until the remaining 80mL of the reaction solution is adjusted to pH=4 to p...

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Abstract

The invention discloses a method for synthesizing cyclic adenosine monophosphate, belonging to the field of nucleoside synthesis in organic chemistry. The reaction steps are as follows: using adenylic acid as a raw material, forming a ring under the action of acetic anhydride in the next step to obtain acetylated cyclic adenosine monophosphate, and then undergoing alkaline hydrolysis to obtain cyclic adenosine monophosphate. The whole process requires only two steps of reaction, and the operation is simple, avoiding the large amount of solvent used in the traditional synthesis process. It has been verified on a kilogram scale and has industrial application prospects.

Description

technical field [0001] The invention belongs to the synthesis of adenine nucleotides in organic chemistry, in particular to a method for synthesizing cyclic adenosine monophosphate. Background technique [0002] Cyclic adenosine monophosphate, chemical name: adenosine-3',5'-cyclic phosphate, CAS number: 60-92-4, molecular formula is C 10 h 12 N 5 o 6 P, as a very important pharmaceutical intermediate, is one of the hot spots of current molecular biology research. Cyclic adenosine monophosphate is closely related to diseases such as psoriasis, coronary heart disease, asthma, hypertension, diabetes and malignant tumors. [0003] Since the 1950s and 1960s, there have been reports on the synthesis of cyclic adenosine monophosphate in domestic and foreign literature, and then different processes have been gradually used to produce cyclic adenosine monophosphate. At present, the methods reported in the literature mainly include: alkaline hydrolysis method, active ester method...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/213C07H1/00
CPCC07H1/00C07H19/213
Inventor 杨西宁李涛卫涛靳海燕刘沛张赛楠刘亚利
Owner TUOXIN GROUP
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