CN109438286A - A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine - Google Patents
A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine Download PDFInfo
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- CN109438286A CN109438286A CN201811627875.9A CN201811627875A CN109438286A CN 109438286 A CN109438286 A CN 109438286A CN 201811627875 A CN201811627875 A CN 201811627875A CN 109438286 A CN109438286 A CN 109438286A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Abstract
The present invention relates to a kind of preparation methods of (S)-N-Boc-3- bromophenyl alanine, the bromo- heptane of 1- amino -2- is added in the reaction vessel, controls mixing speed 255-270rpm, Klorvess Liquid is added in 60-80min, temperature is increased to 50-55 DEG C, maintains 40-55min；Continuously add praseodymium oxide powder, temperature is increased in 3-4h to 60-67 DEG C, then glycerol triacetate solution is added, the reaction was continued 70-100min, reduces temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing is multiple, repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes the washing of 3- hexanone solution in pentaerythrite solution.The present invention adds block reaction rate, greatly shortens the production cycle, while yield can also be made to be greatly improved, and reduces the cost of production.
Description
Technical field
The present invention relates to a kind of preparation methods of (S)-N-Boc-3- bromophenyl alanine.
Background technique
The synthesis of amino acid esters compound and application are a research hotspots in recent years.Since amino-acid ester is with special
Physicochemical property and physiological activity, keep it in an increasingly wide range of applications in industries such as medicine, chemical industry, food, cosmetics.?
In medical industry, amino-acid ester can be used as drug or pharmaceutical intermediate；A variety of amino-acid esters can be used directly or indirectly in and control
Different illnesss is treated, if phenylalanine ester can be antitumor, cysteine lauryl has the curative effects such as anti-inflammatory, analgesic, can be used for treating
Respiratory disease；Amino-acid benzyl base ester is easy to penetrate into red blood cell, and when low concentration can anti-anemia action；A variety of amino-acid esters can be made
For the ingredient of local anesthetic, the side effect of anesthetic is reduced；In the food industry, amino-acid ester can be used as food additives.
Summary of the invention
In order to solve the above technical problems, the object of the present invention is to provide a kind of preparations of (S)-N-Boc-3- bromophenyl alanine
Method.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine, it is characterised in that: 1- ammonia is added in the reaction vessel
The bromo- heptane of base -2- controls mixing speed 255-270rpm, and Klorvess Liquid is added in 60-80min, increases temperature to 50-
55 DEG C, maintain 40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67 DEG C, glycerol three is then added
Acetate solution, the reaction was continued 70-100min reduce temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing repeatedly, 3-
Repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes the washing of hexanone solution in pentaerythrite solution.
Preferably, the Klorvess Liquid mass fraction is 20-30%.
Preferably, the glycerol triacetate liquid quality fraction is 20-25%.
Preferably, the sodium nitrate solution mass fraction is 25-30%.
Preferably, the 3- hexanone liquid quality fraction is 45-50%.
Preferably, the methylphenylamine liquid quality fraction is 62-70%.
Preferably, the pentaerythrite liquid quality fraction is 85-90%.
Preferably, the bromo- heptane of 1- amino -2- is added in the reaction vessel, mixing speed 255-270rpm is controlled, in 60-
Klorvess Liquid is added in 80min, increases temperature to 50-55 DEG C, maintains 40-55min；Praseodymium oxide powder is continuously added, in 3-
Temperature is increased in 4h to 60-67 DEG C, and glycerol triacetate solution is then added, the reaction was continued 70-100min, reduction temperature to 8-
12 DEG C, solution layering, sodium nitrate solution washs repeatedly, and repeatedly, the washing of methylphenylamine solution is multiple for the washing of 3- hexanone solution,
It is recrystallized in pentaerythrite solution.
Preferably, the bromo- heptane of 1- amino -2- is added in the reaction vessel, mixing speed 255-270rpm is controlled, in 60-
Klorvess Liquid is added in 80min, increases temperature to 50-55 DEG C, maintains 40-55min；Praseodymium oxide powder is continuously added, in 3-
Temperature is increased in 4h to 60-67 DEG C, and glycerol triacetate solution is then added, the reaction was continued 70-100min, reduction temperature to 8-
12 DEG C, solution layering, sodium nitrate solution washs repeatedly, and repeatedly, the washing of methylphenylamine solution is multiple for the washing of 3- hexanone solution,
It is recrystallized in pentaerythrite solution.
Preferably, the bromo- heptane of 1- amino -2- is added in the reaction vessel, mixing speed 255-270rpm is controlled, in 60-
Klorvess Liquid is added in 80min, increases temperature to 50-55 DEG C, maintains 40-55min；Praseodymium oxide powder is continuously added, in 3-
Temperature is increased in 4h to 60-67 DEG C, and glycerol triacetate solution is then added, the reaction was continued 70-100min, reduction temperature to 8-
12 DEG C, solution layering, sodium nitrate solution washs repeatedly, and repeatedly, the washing of methylphenylamine solution is multiple for the washing of 3- hexanone solution,
It is recrystallized in pentaerythrite solution.
According to the above aspect of the present invention, the present invention has at least the following advantages:
The present invention adds block reaction rate, greatly shortens the production cycle, while yield can also be made to have obtained biggish mention
Height reduces the cost of production.
The above description is only an overview of the technical scheme of the present invention, in order to better understand the technical means of the present invention,
And can be implemented in accordance with the contents of the specification, with presently preferred embodiments of the present invention, detailed description is as follows below.
Specific embodiment
With reference to embodiment, the embodiment of the present invention is furthur described in detail.Following embodiment is used for
Illustrate the present invention, but is not intended to limit the scope of the invention.
In order to enable those skilled in the art to better understand the solution of the present invention, right below in conjunction with the embodiment of the present invention
Technical solution in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment is only the present invention one
Section Example, instead of all the embodiments.Based on the embodiment of the present invention, those skilled in the art are not making creation
Property labour under the premise of every other embodiment obtained, shall fall within the protection scope of the present invention.
Embodiment
A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine, is added 1- amino -2- bromo- heptan in the reaction vessel
Alkane controls mixing speed 255-270rpm, and Klorvess Liquid is added in 60-80min, increases temperature to 50-55 DEG C, maintains
40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67 DEG C, it is molten that glycerol triacetate is then added
Liquid, the reaction was continued 70-100min reduce temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing repeatedly, 3- hexanone solution
Repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes in pentaerythrite solution for washing.
Embodiment one
A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine, is added 1- amino -2- bromo- heptan in the reaction vessel
Alkane controls mixing speed 255-270rpm, and Klorvess Liquid is added in 60-80min, increases temperature to 50-55 DEG C, maintains
40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67 DEG C, it is molten that glycerol triacetate is then added
Liquid, the reaction was continued 70-100min reduce temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing repeatedly, 3- hexanone solution
Repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes in pentaerythrite solution for washing.
Embodiment two
A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine, is added 1- amino -2- bromo- heptan in the reaction vessel
Alkane controls mixing speed 255-270rpm, and Klorvess Liquid is added in 60-80min, increases temperature to 50-55 DEG C, maintains
40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67 DEG C, it is molten that glycerol triacetate is then added
Liquid, the reaction was continued 70-100min reduce temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing repeatedly, 3- hexanone solution
Repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes in pentaerythrite solution for washing.
Embodiment three
A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine, is added 1- amino -2- bromo- heptan in the reaction vessel
Alkane controls mixing speed 255-270rpm, and Klorvess Liquid is added in 60-80min, increases temperature to 50-55 DEG C, maintains
40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67 DEG C, it is molten that glycerol triacetate is then added
Liquid, the reaction was continued 70-100min reduce temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing repeatedly, 3- hexanone solution
Repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes in pentaerythrite solution for washing.
The above is only a preferred embodiment of the present invention, it is not intended to restrict the invention, it is noted that for this skill
For the those of ordinary skill in art field, without departing from the technical principles of the invention, can also make it is several improvement and
Modification, these improvements and modifications also should be regarded as protection scope of the present invention.
Claims (10)
1. a kind of preparation method of (S)-N-Boc-3- bromophenyl alanine, it is characterised in that: 1- amino-is added in the reaction vessel
The bromo- heptane of 2- controls mixing speed 255-270rpm, and Klorvess Liquid is added in 60-80min, increases temperature to 50-55
DEG C, maintain 40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67 DEG C, three second of glycerol is then added
Acid esters solution, the reaction was continued 70-100min reduce temperature to 8-12 DEG C, solution layering, sodium nitrate solution washing repeatedly, 3- oneself
Repeatedly, the washing of methylphenylamine solution repeatedly, recrystallizes the washing of ketone solution in pentaerythrite solution.
2. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: described
Klorvess Liquid mass fraction be 20-30%.
3. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: described
Glycerol triacetate liquid quality fraction be 20-25%.
4. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: described
Sodium nitrate solution mass fraction be 25-30%.
5. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: described
3- hexanone liquid quality fraction be 45-50%.
6. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: described
Methylphenylamine liquid quality fraction be 62-70%.
7. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: described
Pentaerythrite liquid quality fraction be 85-90%.
8. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: anti-
The addition bromo- heptane of 1- amino -2- in container is answered, mixing speed 255-270rpm is controlled, it is molten that potassium chloride is added in 60-80min
Liquid increases temperature to 50-55 DEG C, maintains 40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67
DEG C, then it is added glycerol triacetate solution, the reaction was continued 70-100min reduces temperature to 8-12 DEG C, solution layering, nitric acid
Repeatedly, the washing of 3- hexanone solution repeatedly, repeatedly, tie again in pentaerythrite solution by the washing of methylphenylamine solution for sodium solution washing
It is brilliant.
9. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that: anti-
The addition bromo- heptane of 1- amino -2- in container is answered, mixing speed 255-270rpm is controlled, it is molten that potassium chloride is added in 60-80min
Liquid increases temperature to 50-55 DEG C, maintains 40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-67
DEG C, then it is added glycerol triacetate solution, the reaction was continued 70-100min reduces temperature to 8-12 DEG C, solution layering, nitric acid
Repeatedly, the washing of 3- hexanone solution repeatedly, repeatedly, tie again in pentaerythrite solution by the washing of methylphenylamine solution for sodium solution washing
It is brilliant.
10. the preparation method of one kind (S)-N-Boc-3- bromophenyl alanine according to claim 1, it is characterised in that:
The bromo- heptane of 1- amino -2- is added in reaction vessel, controls mixing speed 255-270rpm, potassium chloride is added in 60-80min
Solution increases temperature to 50-55 DEG C, maintains 40-55min；Praseodymium oxide powder is continuously added, temperature is increased in 3-4h to 60-
67 DEG C, then it is added glycerol triacetate solution, the reaction was continued 70-100min reduces temperature to 8-12 DEG C, solution layering, nitre
Repeatedly, repeatedly, methylphenylamine solution washs repeatedly the washing of 3- hexanone solution, the weight in pentaerythrite solution for acid sodium solution washing
Crystallization.
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| CN201811627875.9A CN109438286A (en) | 2018-12-28 | 2018-12-28 | A kind of preparation method of (S)-N-Boc-3- bromophenyl alanine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108238925A (en) * | 2017-08-19 | 2018-07-03 | 成都千叶龙华石油工程技术咨询有限公司 | The synthetic method of organic synthesis intermediate caproic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108238925A (en) * | 2017-08-19 | 2018-07-03 | 成都千叶龙华石油工程技术咨询有限公司 | The synthetic method of organic synthesis intermediate caproic acid |
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