CN113861094A - Preparation method of 3-maleimide propionic acid - Google Patents
Preparation method of 3-maleimide propionic acid Download PDFInfo
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- CN113861094A CN113861094A CN202111338688.0A CN202111338688A CN113861094A CN 113861094 A CN113861094 A CN 113861094A CN 202111338688 A CN202111338688 A CN 202111338688A CN 113861094 A CN113861094 A CN 113861094A
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- beta
- alanine
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- propionic acid
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- WCILBWLDYPEMNA-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-3-yl)propanoic acid Chemical compound OC(=O)CCC1=CC(=O)NC1=O WCILBWLDYPEMNA-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 61
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000001816 cooling Methods 0.000 claims abstract description 24
- 229940000635 beta-alanine Drugs 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000003756 stirring Methods 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 18
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 15
- 239000013078 crystal Substances 0.000 claims abstract description 15
- 238000001914 filtration Methods 0.000 claims abstract description 13
- 229960000583 acetic acid Drugs 0.000 claims abstract description 12
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 12
- 238000005917 acylation reaction Methods 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 230000018044 dehydration Effects 0.000 claims abstract description 7
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 7
- 238000007670 refining Methods 0.000 claims abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 229940044600 maleic anhydride Drugs 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- IUTPJBLLJJNPAJ-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-1-yl)propanoic acid Chemical compound OC(=O)CCN1C(=O)C=CC1=O IUTPJBLLJJNPAJ-UHFFFAOYSA-N 0.000 claims 6
- 241000953555 Theama Species 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 13
- 238000005070 sampling Methods 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 3-maleimide propionic acid, belonging to the technical field of chemical synthesis and comprising the following steps: adding anhydrous glacial acetic acid into a reaction bottle, sequentially adding maleic anhydride and beta-alanine, stirring and dissolving to perform acylation reaction; when the beta-alanine residue in the feed liquid is less than 1 percent, the reaction is finished; cooling the feed liquid to prepare an AMA intermediate; putting the AMA intermediate into toluene, heating, carrying out reflux dehydration, cooling when no water flows out, and carrying out high vacuum reduced pressure distillation to remove the toluene; adding seed crystal, cooling, stirring until crystal is separated out, filtering to obtain crude product, and refining to obtain the final product. The method has the characteristics of wide raw material source, simple operation, high yield and less impurities, solves the problem of no crystal type 3-maleimide propionic acid, and is convenient to popularize and apply.
Description
Technical Field
The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of 3-maleimide propionic acid.
Background
The molecular formula of the 3-maleimide propionic acid is C7H7NO4, is a monomer with an unsaturated imide ring-packed structure, is a modifier of a functional polymer material, is mainly used for synthesizing a key intermediate of an anti-infection biochemical reagent in the emerging biological field, and is also used for a targeted drug carrier; is widely used in the fields of chemical industry, medical intermediates, dyes and the like. At present, the existing process for preparing 3-maleimide propionic acid has low yield and more impurities.
Disclosure of Invention
The invention aims to provide a preparation method of 3-maleimide propionic acid, and aims to solve the technical problems of low yield and more impurities in the process for preparing the 3-maleimide propionic acid in the prior art.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a preparation method of 3-maleimide propionic acid comprises the following steps:
under the condition of room temperature, adding anhydrous glacial acetic acid into a reaction bottle, sequentially adding maleic anhydride and beta-alanine, stirring and dissolving, and controlling the reaction temperature to be 30 +/-5 ℃; the addition amount of each component is as follows:
anhydrous glacial acetic acid, maleic anhydride and beta-alanine are added in sequence, wherein the dosage of the glacial acetic acid is 3-5 times of the mass sum of the maleic anhydride and the beta-alanine, and the weight ratio of the maleic anhydride: beta-alanine molar ratio = (1-1.21): 1;
starting to sample and detect the residual amount of the beta-alanine after 5 hours of reaction until the residual amount of the beta-alanine in the acylation reaction is less than 1 percent and the reaction is finished; cooling the feed liquid to prepare an allyl methacrylate intermediate;
putting the allyl methacrylate intermediate into a polar solvent with the volume 12-30 times of that of the allyl methacrylate intermediate, filling protective gas, dropwise adding a catalyst, controlling the temperature of feed liquid at 95-130 ℃, and performing reflux dehydration;
when no water flows out, the temperature is reduced to 40-90 ℃, and high vacuum reduced pressure distillation is carried out to remove the polar solvent;
dripping 0.1 times of water by weight into the distilled feed liquid, cooling, adding seed crystals, continuously stirring and cooling to separate out crystals, and filtering to obtain a crude product of the 3-maleimide propionic acid;
and (3) putting the obtained crude product into an extracting agent for refining to obtain a finished product of the 3-maleimide propionic acid.
Preferably, the reaction bottle is a three-mouth bottle, a stirring device is arranged at the middle bottle opening of the three-mouth bottle, the bottle opening at one side is connected with the backflow water distribution device, and a thermometer is inserted into the bottle opening at the other side.
Preferably, the allyl methacrylate intermediate can be obtained by filtration to obtain a wet powder, or after distillation.
Preferably, the protective gas is nitrogen.
Preferably, the polar solvent is toluene, ethyl acetate or butyl acetate.
Preferably, the catalyst is triethylamine, concentrated sulfuric acid, trimethylamine, pyridine, dimethylamine or methylamine, and the dosage of the catalyst is 0.5 to 5 percent of the weight of the allyl methacrylate intermediate.
Preferably, the extractant is methanol, ethanol or isopropanol, and the dosage of the extractant is 8-20 times of the weight of the crude product of the 3-maleimide propionic acid.
Adopt the produced beneficial effect of above-mentioned technical scheme to lie in: compared with the prior art, the invention obtains the crystalline 3-maleimide propionic acid through acylation reaction, dehydration and crystallization, has the characteristics of wide raw material source, simple operation and less impurities, solves the problem of no crystalline 3-maleimide propionic acid, and is convenient to popularize and apply.
Detailed Description
The technical solutions in the embodiments are clearly and completely described below in conjunction with the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a preparation method of 3-maleimide propionic acid, which comprises the following steps:
under the condition of room temperature, adding anhydrous glacial acetic acid into a reaction bottle, sequentially adding maleic anhydride and beta-alanine, stirring and dissolving, and controlling the reaction temperature to be 30 +/-5 ℃; the addition amount of the anhydrous glacial acetic acid is 3-5 times of the total mass of the maleic anhydride and the beta-alanine;
the reaction bottle adopts a three-mouth bottle, the middle bottle mouth of the three-mouth bottle is provided with a stirring device, the bottle mouth at one side is connected with the backflow water dividing device, and the bottle mouth at the other side is inserted with a thermometer.
After the feed liquid in the three-mouth bottle reacts for 5 hours, sampling and detecting the residual amount of the beta-alanine, and reacting until the residual amount of the beta-alanine in the acylation reaction is less than 1 percent and the reaction is finished; cooling the feed liquid to prepare an Allyl Methacrylate (AMA) intermediate;
putting allyl methacrylate into toluene 12-30 times of the allyl methacrylate, dropwise adding triethylamine 0.5-5% of the weight of an Allyl Methacrylate (AMA) intermediate under the protection of nitrogen, and controlling the temperature to 95-130 ℃ for reflux dehydration; wherein, the toluene can be replaced by an ethyl acetate bag or a butyl acetate bag; the triethylamine can be replaced by concentrated sulfuric acid, trimethylamine, pyridine, dimethylamine or methylamine;
when no water flows out from the water separator of the reflux water separator, the temperature is reduced to 40-90 ℃, and high vacuum reduced pressure distillation is carried out to remove toluene; after the toluene is evaporated to dryness, continuously adding the same amount of toluene to carry out secondary high vacuum distillation to obtain oily liquid; dripping 0.1 times of water by weight into the obtained oily liquid, cooling, adding seed crystals, continuously stirring and cooling, separating out crystals, and filtering to obtain a crude product of the 3-maleimide propionic acid;
and (3) putting the obtained crude product into 0.1 weight time of water methanol, and refining to obtain the finished product of the 3-maleimide propionic acid. The methanol can be replaced by ethanol or isopropanol.
Wherein the Allyl Methacrylate (AMA) intermediate can be obtained by filtering to obtain wet powder or distilling.
The following are several specific examples:
example one
Adding 207.5ml of anhydrous glacial acetic acid into a three-neck flask at room temperature, sequentially adding 23.7g of maleic anhydride and 17.8g of beta-alanine, starting a stirring device to stir and dissolve the maleic anhydride and the beta-alanine in a uniform state, and controlling the reaction temperature to be 25 ℃. And (5) starting to perform reaction for 5 hours, sampling and detecting the beta-alanine residue until the beta-alanine residue in the acylation reaction is less than 1.0%, and cooling and filtering after the reaction is finished to obtain the AMA intermediate.
Adding AMA into 21 times of toluene, dropwise adding triethylamine with the weight of 5% of AMA under the protection of nitrogen, controlling the temperature to be 115 ℃, refluxing and dehydrating, and cooling and controlling the temperature to be 90 ℃ to perform high vacuum reduced pressure distillation to remove the toluene until no water flows out of a water separator; after the toluene is evaporated to dryness, continuing adding 9 times of toluene to carry out secondary high vacuum distillation to obtain oily liquid. And dropwise adding a small amount of water into the obtained liquid, cooling, adding seed crystals, continuously stirring and cooling, separating out crystals, and filtering to obtain a crude product of the 3-maleimide propionic acid. And (3) putting the obtained crude product into methanol for refining to obtain a finished product of the 3-maleimide propionic acid.
Example two
Adding 186.6ml of anhydrous glacial acetic acid into a three-necked bottle at room temperature, sequentially adding 35.5g of maleic anhydride and 26.7g of beta-alanine, starting a stirring device to stir and dissolve the maleic anhydride and the beta-alanine in a uniform state, and controlling the reaction temperature to be 25 ℃. And (5) starting to perform reaction for 5 hours, sampling and detecting the beta-alanine residue until the beta-alanine residue in the acylation reaction is less than 1.0%, and cooling and filtering after the reaction is finished to obtain the AMA intermediate.
Adding AMA into 8 times of toluene, dropwise adding triethylamine with the weight of 3% of AMA under the protection of nitrogen, controlling the temperature to be 115 ℃ for reflux dehydration, cooling and controlling the temperature to be 90 ℃ for high vacuum reduced pressure distillation to remove toluene until no water flows out of a water separator, and continuously adding 8 times of toluene for secondary high vacuum distillation after the toluene is evaporated to dryness to obtain oily liquid. And dropwise adding a small amount of water into the obtained liquid, cooling, adding seed crystals, continuously stirring and cooling, separating out crystals, and filtering to obtain a crude product of the 3-maleimide propionic acid. And (3) putting the obtained crude product into methanol for refining to obtain a finished product of the 3-maleimide propionic acid.
Example three:
adding 369ml of anhydrous glacial acetic acid into a three-necked bottle at room temperature, sequentially adding 39.2g of maleic anhydride and 35.6g of beta-alanine, starting a stirring device to stir and dissolve the maleic anhydride and the beta-alanine in a uniform state, and controlling the reaction temperature to be 30 ℃. And (5) starting to perform reaction for 5 hours, sampling and detecting the beta-alanine residue until the beta-alanine residue in the acylation reaction is less than 1.0%, and cooling and filtering after the reaction is finished to obtain the AMA intermediate.
Adding AMA into 10 times of toluene, dropwise adding 5% triethylamine under the protection of nitrogen, controlling the temperature to 130 ℃ for reflux dehydration, cooling and controlling the temperature to 60 ℃ until no water flows out of a water separator, carrying out high vacuum reduced pressure distillation to remove toluene, evaporating the toluene to dryness, and continuously adding equivalent toluene to carry out secondary high vacuum distillation to obtain oily liquid. Adding water into the obtained liquid for cooling, adding seed crystals, continuously stirring for cooling, separating out crystals, and filtering to obtain a crude product of the 3-maleimide propionic acid. And (3) putting the obtained crude product into methanol for refining to obtain a finished product of the 3-maleimide propionic acid.
In the description above, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways than those specifically described and will be readily apparent to those of ordinary skill in the art without departing from the spirit of the present invention, and thus the present invention is not limited to the specific embodiments disclosed above.
Claims (7)
1. A preparation method of 3-maleimide propionic acid is characterized by comprising the following steps:
under the condition of room temperature, adding anhydrous glacial acetic acid into a reaction bottle, sequentially adding maleic anhydride and beta-alanine, stirring and dissolving, and controlling the reaction temperature to be 30 +/-5 ℃; the addition amount of each component is as follows:
anhydrous glacial acetic acid, maleic anhydride and beta-alanine are added in sequence, wherein the dosage of the glacial acetic acid is 3-5 times of the mass sum of the maleic anhydride and the beta-alanine, and the weight ratio of the maleic anhydride: beta-alanine molar ratio = (1-1.21): 1;
starting to sample and detect the residual amount of the beta-alanine after 5 hours of reaction until the residual amount of the beta-alanine in the acylation reaction is less than 1 percent and the reaction is finished; cooling the feed liquid to prepare an allyl methacrylate intermediate;
putting the allyl methacrylate intermediate into a polar solvent with the volume 12-30 times of that of the allyl methacrylate intermediate, filling protective gas, dropwise adding a catalyst, controlling the temperature of feed liquid at 95-130 ℃, and performing reflux dehydration;
when no water flows out, the temperature is reduced to 40-90 ℃, and high vacuum reduced pressure distillation is carried out to remove the polar solvent;
dripping 0.1 times of water by weight into the distilled feed liquid, cooling, adding seed crystals, continuously stirring and cooling to separate out crystals, and filtering to obtain a crude product of the 3-maleimide propionic acid;
and (3) putting the obtained crude product into an extracting agent for refining to obtain a finished product of the 3-maleimide propionic acid.
2. The method for producing 3-maleimidopropionic acid according to claim 1, wherein: the reaction bottle is a three-mouth bottle, a stirring device is arranged at the middle bottle opening of the three-mouth bottle, the bottle opening at one side is connected with the backflow water distribution device, and a thermometer is inserted into the bottle opening at the other side.
3. The method for producing 3-maleimidopropionic acid according to claim 1, wherein: the allyl methacrylate intermediate can be obtained by filtering to obtain wet powder or distilling to obtain the allyl methacrylate intermediate.
4. The method for producing 3-maleimidopropionic acid according to claim 1, wherein: the protective gas is nitrogen.
5. The method for producing 3-maleimidopropionic acid according to claim 1, wherein: the polar solvent is toluene, ethyl acetate or butyl acetate.
6. The method for producing 3-maleimidopropionic acid according to claim 1, wherein: the catalyst is triethylamine, concentrated sulfuric acid, trimethylamine, pyridine, dimethylamine or methylamine, and the dosage of the catalyst is 0.5 to 5 percent of the weight of the allyl methacrylate intermediate.
7. The method for producing 3-maleimidopropionic acid according to claim 1, wherein: the extractant is methanol, ethanol or isopropanol, and the dosage of the extractant is 8-20 times of the weight of the crude product of the 3-maleimide propionic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111338688.0A CN113861094A (en) | 2021-11-12 | 2021-11-12 | Preparation method of 3-maleimide propionic acid |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111338688.0A CN113861094A (en) | 2021-11-12 | 2021-11-12 | Preparation method of 3-maleimide propionic acid |
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| CN113861094A true CN113861094A (en) | 2021-12-31 |
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| CN202111338688.0A Pending CN113861094A (en) | 2021-11-12 | 2021-11-12 | Preparation method of 3-maleimide propionic acid |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007284643A (en) * | 2006-04-20 | 2007-11-01 | Nec Corp | Polyfunctional maleimide compound, method for producing the same and shape memory resin containing the same |
| CN102180963A (en) * | 2011-04-22 | 2011-09-14 | 中国药科大学 | Glucagons like peptide-1 (GLP-1) analog and application thereof |
| CN102363607A (en) * | 2011-11-28 | 2012-02-29 | 中国科学院上海有机化学研究所 | Method for synthesizing maleimide by using strongly acidic room-temperature ionic liquid as medium |
| CN107236055A (en) * | 2017-05-19 | 2017-10-10 | 华东师范大学 | A kind of new glucan derivative and its application |
-
2021
- 2021-11-12 CN CN202111338688.0A patent/CN113861094A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007284643A (en) * | 2006-04-20 | 2007-11-01 | Nec Corp | Polyfunctional maleimide compound, method for producing the same and shape memory resin containing the same |
| CN102180963A (en) * | 2011-04-22 | 2011-09-14 | 中国药科大学 | Glucagons like peptide-1 (GLP-1) analog and application thereof |
| CN102363607A (en) * | 2011-11-28 | 2012-02-29 | 中国科学院上海有机化学研究所 | Method for synthesizing maleimide by using strongly acidic room-temperature ionic liquid as medium |
| CN107236055A (en) * | 2017-05-19 | 2017-10-10 | 华东师范大学 | A kind of new glucan derivative and its application |
Non-Patent Citations (4)
| Title |
|---|
| DANIEL H. RICH等: "Alkylating derivatives of amino acids and peptides. Synthesis of N-maleoylamino acids, [1-(N-maleoylglycyl)cysteinyl]oxytocin, and [1-(N-maleoyl-11-aminoundecanoyl)cysteinyl]oxytocin. Effects on vasopressin-stimulated water loss from isolated toad bladder", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
| KENNETH CHRISTOPHER KOEHLER等: "Kinetic and Thermodynamic Measurements for the Facile Property Prediction of Diels–Alder-Conjugated Material Behavior", 《AICHE JOURNAL》 * |
| PAVEL VEPREK等: "Comblike Dendrimers Containing Tn Antigen Modulate Natural Killing and Induce the Production of Tn Specific Antibodies", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
| RENATA MARCIA DE FIGUEIREDO等: "Synthesis of 4-Maleimidobutyric Acid and Related Maleimides", 《SYNTHESIS》 * |
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Application publication date: 20211231 |