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Synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester

A technology of phthaloyl p-phenylalanine ethyl ester, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of long synthetic route, low yield, high toxicity, etc., and achieve high overall yield and high safety , the effect of stable quality

Inactive Publication Date: 2016-11-09
王剑
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] What the present invention will solve is the long synthetic route, high cost, low yield and toxicity existing in the existing N-phthaloyl p-(dihydroxyethyl)amino-L-phenylalanine ethyl ester synthesis process Large and other disadvantages

Method used

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  • Synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester
  • Synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester

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Effect test

Embodiment 1

[0027] A kind of synthetic technique of N-phthaloyl p-(dihydroxyethyl) amino-L-phenylalanine ethyl ester, the concrete steps of described technique are as follows:

[0028] (1) Amino protection reaction:

[0029] In a three-necked flask, add 120 grams of p-nitro-L-phenylalanine hydrate, 500 milliliters of toluene and 100 milliliters of triethylamine to mix, add 85 grams of phthalic anhydride under stirring, heat to reflux, and react 3 Hour, after reaction finishes, be cooled to room temperature, the reaction solution that obtains is poured in the hydrochloric acid solution, after fully stirring, filter and obtain 158 gram N-phthaloyl p-nitro-L-phenylalanine solids, the step The yield is 90%.

[0030] (2) Esterification reaction:

[0031] Get 100 grams of N-phthaloyl-p-nitro-L-phenylalanine and 500 milliliters of ethanol and mix them in a three-necked flask, add 80 grams of thionyl chloride dropwise while stirring, and heat to Reflux, react for 3 hours, cool to room temperat...

Embodiment 2

[0038] The synthetic technique of N-phthaloyl p-(dihydroxyethyl) amino-L-phenylalanine ethyl ester, described technique comprises the following steps:

[0039] (1) Amino protection reaction: dissolve the hydrate of raw material p-nitro-L-phenylalanine with solvent and triethylamine, add phthalic anhydride in the obtained raw material mixture, heat and reflux for reaction, and the obtained reaction The liquid is poured into the hydrochloric acid solution, and after fully stirring, N-phthaloyl-p-nitro-L-phenylalanine is obtained;

[0040] (2) Esterification reaction: dissolve the product obtained in step 1 with ethanol, add a chlorinating agent to the obtained mixed solution, and heat to reflux for reaction to obtain N-phthaloyl-p-nitro-L-phenylalanine ethyl ester;

[0041] (3) Reduction reaction: Dissolve the product obtained in step 2 with a solvent, place the obtained mixed solution in a reactor, add a catalyst to the reactor, and feed hydrogen gas under certain conditions t...

Embodiment 3

[0053] The synthetic technique of N-phthaloyl p-(dihydroxyethyl) amino-L-phenylalanine ethyl ester, described technique comprises the following steps:

[0054] (1) Amino protection reaction: dissolve the hydrate of raw material p-nitro-L-phenylalanine with solvent and triethylamine, add phthalic anhydride in the obtained raw material mixture, heat and reflux for reaction, and the obtained reaction The liquid is poured into the hydrochloric acid solution, and after fully stirring, N-phthaloyl-p-nitro-L-phenylalanine is obtained;

[0055] (2) Esterification reaction: dissolve the product obtained in step 1 with ethanol, add a chlorinating agent to the obtained mixed solution, and heat to reflux for reaction to obtain N-phthaloyl-p-nitro-L-phenylalanine ethyl ester;

[0056] (3) Reduction reaction: dissolve the product obtained in step 2 with a solvent, place the obtained mixed solution in a reactor, add a catalyst to the reactor, and feed hydrogen gas under certain conditions t...

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Abstract

The invention provides a synthesis process of N-paraphthalyl(diethanol)amino-L-phenylalanine ethyl ester. The process includes the first step of amino protection reaction, the second step of esterification reaction, the third step of reduction reaction and the fourth step of substitution reaction. According to the synthesis process, amino is protected by phthalic anhydride, and then esterification, reduction and substitution are conducted obtain the product. The process has the advantages of being low in cost, mild in reaction condition, low in toxicity, convenient to operate, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis process of N-phthaloyl p-(dihydroxyethyl)amino-L-phenylalanine ethyl ester, belonging to the field of synthesis of pharmaceutical intermediates. Background technique [0002] N-phthaloyl p-(dihydroxyethyl) amino-L-phenylalanine ethyl ester, its structural formula is: [0003] [0004] N-phthaloyl-p-(dihydroxyethyl)amino-L-phenylalanine ethyl ester is an intermediate of antineoplastic drug melphalan, which is a cycle non-specific antineoplastic Due to the specificity of its structure, the drug can enter the tumor cells and take effect, leading to the death of tumor cells, thereby playing an anti-tumor effect. It has been clinically proven that melphalan can be used to treat multiple myeloma, breast cancer, ovarian cancer, chronic lymphocytic and granulocytic leukemia, malignant lymphoma, multiple myeloma, malignant melanoma, osteosarcoma and soft tissue tumors, etc. The application is very extensive, and the eff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 王健
Owner 王剑
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