Synthesis method for 2-carboxyphenylboronic acid
A carboxyphenylboronic acid and synthesis method technology, applied in the field of chemical synthesis, can solve problems such as insufficient uniformity and strict temperature control, and achieve the effects of reasonable process design, increased loading capacity, and replacement efficiency
Inactive Publication Date: 2016-09-21
XUCHANG HAOFENG CHEM TECH
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Problems solved by technology
[0002] At present, carboxyphenylboronic acid is an important intermediate in drug synthesis, and various synthetic reactions are becoming more and more common; there are many kinds of phenylboronic acid derivatives, and their development is very fast. In recent years, they have been widely used in electronics, chemistry, medicine, biology and other fields. , such as liquid crystal display materials, chemiluminescent enhancers, wood preservatives and enzyme inhibitors, in addition it can selectively promote the transport of glucose through the lipid bilayer, and is currently being increasingly used as a molecular recognition unit, In particular, it is used to design and synthesize boron lectins (glycoproteins) and carbohydrate sensors; phenylboronic acid (phenylboronic acid) derivatives have two forms, charged and uncharged, in aqueous solution, of which only the charged The form can form reversible five-membered or six-membered cyclic esters with polyols having 1,2- or 1,3-diol groups; this process is reversible, and there are a large number of such polyols in nature, For example, polysaccharides and other substances, many of them exist in organisms and have an important impact on the life activities of organisms; phenylboronic acid is a chemical product with a molecular weight of 121.93; English name: Phenylboronic Acid; phenylboronic acid is used as a Suzuki diaryl cross The boronic acid component in coupling research; it is used in Stille and Suzuki cross-coupling reactions; the existing phenylboronic acid has many existing experimental results and a high success rate when it is synthesized, but when it is actually put into production, there are many problems, large-scale The temperature cannot be strictly controlled during production, which will lead to the synthesis effect. In addition, when adding reagents in production, the uniformity is not enough. These have a lot to do with the reagents added to the synthesis. Therefore, reagents are the focus of urgent improvement
Method used
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Experimental program
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Embodiment Construction
[0015] This specific embodiment adopts following technical scheme: it comprises the following steps:
[0016] 1. Introduce the solvent containing active groups such as hydroxyl into the polymer;
[0017] 2. There are blunting groups such as nitro group connected to the benzene ring, which should be initially synthesized to form another polymer, and the temperature should be kept between -10°C and 2°C;
[0018] 3. Compared with alkyl / alkoxyphenylboronic acid, confirm the proportion of reagents to be added in the next step;
[0019] 4. Add polyhydroxy compound, control the temperature between 10-20 degrees, and adjust the pH value of the side to keep it between 2-5 to obtain a gel;
[0020] 5. Amino groups are introduced into the gel to improve the loading capacity and stability of insulin.
[0021] As a preference, in the step 2, the substituent phenylboronic acid containing active groups such as hydroxyl groups is converted by means of protecting groups and groups.
[0022]...
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The invention discloses a synthesis method for 2-carboxyphenylboronic acid, and belongs to the technical field of chemical synthesis. The synthesis method includes the following steps that 1, a solvent with active groups such as hydroxyl is introduced into a polymer; 2, passivation groups such as nitro are connected to benzene rings, primary synthesis is carried out, another polymer is formed, and temperature is kept ranging from -10 DEG C to -2 DEG C; 3, comparison is conducted with alkyl / alkoxy-phenylboronic acid to determine the proportion of a reagent added in the next step; 4, polyol is added for cooperation, the temperature is kept ranging from 10 DEG C to 20 DEG C, the PH value is adjusted to be kept ranging from 2 to 5, and gel is obtained. The synthesis method is reasonable in flow design and convenient to operate; sudden changes of temperature can be buffered in cooperation with benzene rings, and the problems in the prior art are solved accordingly; under the control over temperature and the PH value, the defects in the present technology can be buffered, efficiency is greatly improved, and production and processing are also promoted.
Description
technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing 2-carboxyphenylboronic acid. Background technique [0002] At present, carboxyphenylboronic acid is an important intermediate in drug synthesis, and various synthetic reactions are becoming more and more common; there are many kinds of phenylboronic acid derivatives, and their development is very fast. In recent years, they have been widely used in electronics, chemistry, medicine, biology and other fields. , such as liquid crystal display materials, chemiluminescent enhancers, wood preservatives and enzyme inhibitors, in addition it can selectively promote the transport of glucose through the lipid bilayer, and is currently being increasingly used as a molecular recognition unit, In particular, it is used to design and synthesize boron lectins (glycoproteins) and carbohydrate sensors; phenylboronic acid (phenylboronic acid) derivatives have t...
Claims
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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 骆俊
Owner XUCHANG HAOFENG CHEM TECH