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Synthesis method of calcium ion selective chelating agents

A synthetic method and selective technology, applied in the field of synthesis of calcium ion selective chelating agent, can solve the problems of cumbersome steps, low product purity and yield

Inactive Publication Date: 2012-08-01
SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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Problems solved by technology

[0010] The above method has the problems of cumbersome steps, low product purity and yield

Method used

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  • Synthesis method of calcium ion selective chelating agents
  • Synthesis method of calcium ion selective chelating agents
  • Synthesis method of calcium ion selective chelating agents

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Embodiment Construction

[0020] The synthetic method of compound 1a comprises the following steps:

[0021] 1. The synthetic reaction steps of compound 1a:

[0022] The first step: add 19.52g (80mmol) 1,2-bis(2-aminophenoxy)ethane, 3.344g (62.4mmol) anhydrous sodium iodide, 72ml (416mmol) of diisopropylethylamine and 120ml of acetonitrile.

[0023] The second step: Slowly heat up and stir. The temperature of the internal bath was raised to 55°C, and 38.4ml (416mmol) of methyl bromoacetate was added dropwise at a constant speed.

[0024] Step 3: after the dropwise addition, the system is filled with nitrogen and sealed, and the temperature is raised to 80° C. in the system again, and then refluxed for 20 hours.

[0025] 2. Post-processing steps for compound 1a synthesis

[0026] Step 4: After the reflux is completed, add 140ml of toluene into the four-neck flask, stir for 30 minutes, and then let stand for 30 minutes. After standing, pour the upper clear layer into a 500ml beaker, add 50ml of tolu...

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Abstract

The invention provides a synthesis method of calcium ion selective chelating agents and relates to a synthesis method of biological medicaments. According to the synthesis method, 1, 2-bi(2-aminophenoxy) ethane is used as raw materials to take two steps of reaction: esterification reaction and acidification reaction, 2-bi(2-aminophenoxy) ethane-N, N, N', N'-quadrol(2a, BAPTA) is synthesized, and the structure of compounds 2a is shown by IR, 1HNMR. Through regulating the mixture ratio and the catalyst consumption, the mol ratio of 1, 2-bi(2-aminophenoxy) ethane to methyl bromoacetate to diisopropylethylamine is 1:5.2:5.2, the yield of the 2-bi(2-aminophenoxy) ethane-N, N, N', N'-quadrol methyl ester(1a, BAPTA methyl ester) is 86 percent, and the purity is 97.45 percent. A chemical purification method is adopted, the BAPTA purity can reach 99 percent, and the yield can reach 94 percent at the purity. The method has the advantages that the production cost is reduced, the process steps are optimized, and in addition, the quality and the yield are improved.

Description

technical field [0001] The invention relates to a synthesis method of a biological medicine, in particular to a synthesis method of a calcium ion selective chelating agent. Background technique [0002] 2-bis(2-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid 2a (O,O'-Bis(2-aminophenyl)ethyleneglycol-N,N,N',N' -tetraacetic acid), referred to as BAPTA, is a non-toxic calcium ion selective chelator and indicator. Its basic chelating unit is similar to EDTA except that two aliphatic nitrogens are replaced by aromatic nitrogens. Therefore, BAPTA is not protonated at physiological pH. The pKa3 of BAPTA is 5.47, and the pKa4 is 6.36. This feature shows that the deprotonation step is not involved in the Ca chelation step. Since it is not interfered by protons, its chelation rate is much higher than that of EGTA. [0003] In 1980, Tsien et al. proposed the introduction of an aromatic chromophore (namely BAPTA) into EDTA based on the optimal structure for calcium ions. The introdu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/18C07C227/18C07C227/40
Inventor 滕雅娣张大伟管国生曲晓晔
Owner SHENYANG INSTITUTE OF CHEMICAL TECHNOLOGY
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