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Preparation method of N-(4-aminobenzoyl)-L-glutamic acid

A technology of aminobenzoyl and nitrobenzoic acid, which is applied in the field of preparation of N--L-glutamic acid, can solve the problems such as difficulty in yield and product quality, high cost, complicated process, etc., and save energy. and production costs, the effect of improving the recovery rate

Inactive Publication Date: 2018-12-21
ABA CHEM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the deficiencies of the prior art, the present invention provides a kind of N-(4-aminobenzoyl)-L-glutamic acid, which has the advantages of simple operation, high yield and low cost, and solves the problem of high cost, It makes it difficult for the final product to meet the needs of market competition, and the yield and product quality are difficult to meet the requirements, and the process is complicated

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A kind of N-(4-aminobenzoyl)-L-glutamic acid, comprising the following raw materials in proportions by weight: 10 parts of nitrobenzoic acid, 15 parts of thionyl chloride, 4 parts of nitrobenzoyl chloride , 10 parts of ammonia water, 10 parts of ethanol, 3 parts of water, 4 parts of glutamine, and 10 parts of aminobenzoyl.

[0025] A kind of preparation method of N-(4-aminobenzoyl)-L-glutamic acid is characterized in that, comprises the following steps:

[0026] 1) nitrobenzoic acid is weighed as 10 parts, thionyl chloride is weighed as 15 parts, nitrobenzoic acid and thionyl chloride are successively added in the reaction vessel for reaction, and the reaction vessel is heated to 50- 60°C, and continue to heat for 1-2 hours. During the heating process of the reaction vessel, the reaction vessel needs to be covered, and the interior of the reaction vessel should be continuously stirred at a constant speed to ensure that the nitrobenzoic acid and thionyl chloride The res...

Embodiment 2

[0032] A kind of N-(4-aminobenzoyl)-L-glutamic acid, comprising the following raw materials in parts by weight: 5 parts of nitrobenzoic acid, 10 parts of thionyl chloride, 2 parts of nitrobenzoyl chloride , 8 parts of ammonia water, 5 parts of ethanol, 2 parts of water, 2 parts of glutamine, and 8 parts of aminobenzoyl.

[0033] A kind of preparation method of N-(4-aminobenzoyl)-L-glutamic acid is characterized in that, comprises the following steps:

[0034] 1) nitrobenzoic acid is weighed as 5 parts, thionyl chloride is weighed as 10 parts, nitrobenzoic acid and thionyl chloride are successively added in the reaction vessel for reaction, and the reaction vessel is heated to 50- 60°C, and continue to heat for 1-2 hours. During the heating process of the reaction vessel, the reaction vessel needs to be covered, and the interior of the reaction vessel should be continuously stirred at a constant speed to ensure that the nitrobenzoic acid and thionyl chloride The response is un...

Embodiment 3

[0040] A kind of N-(4-aminobenzoyl)-L-glutamic acid, comprising the following raw materials in parts by weight: 8 parts of nitrobenzoic acid, 13 parts of thionyl chloride, 3 parts of nitrobenzoyl chloride , 9 parts of ammonia water, 8 parts of ethanol, 2.5 parts of water, 3 parts of glutamine, and 9 parts of aminobenzoyl.

[0041] A kind of preparation method of N-(4-aminobenzoyl)-L-glutamic acid is characterized in that, comprises the following steps:

[0042] 1) nitrobenzoic acid is weighed as 8 parts, and thionyl chloride is weighed as 13 parts, and nitrobenzoic acid and thionyl chloride are successively added to the reaction vessel for reaction, and the reaction vessel is heated to 50- 60°C, and continue to heat for 1-2 hours. During the heating process of the reaction vessel, the reaction vessel needs to be covered, and the interior of the reaction vessel should be continuously stirred at a constant speed to ensure that the nitrobenzoic acid and thionyl chloride The resp...

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Abstract

The invention relates to the technical field of medicinal intermediates, and discloses N-(4-aminobenzoyl)-L-glutamic acid. The N-(4-aminobenzoyl)-L-glutamic acid comprises the following raw materialsin parts by weight: 5-10 parts of nitrobenzoic acid, 10-15 parts of sulfoxide chloride, 2-4 parts of nitrobenzoyl chloride, 8-10 parts of ammonia water, 5-10 parts of ethanol, 2-3 parts of water, 2-4parts of glutamic acid and 8-10 parts of aminobenzoyl. According to the N-(4-aminobenzoyl)-L-glutamic acid, the nitrobenzoic acid and the sulfoxide chloride are placed in a reaction container and heated and the nitrobenzoic acid reacts with the sulfoxide chloride; the nitrobenzoic acid is in a form of a light yellow crystal, o-nitrobenzoic acid and p-nitrobenzoic acid are prepared by oxidizing corresponding nitrotoluene, m-nitrobenzoic acid is prepared by directly nitrating benzoic acid, and the nitrobenzoic acid is used as a chemical raw material and an analytical reagent for dyes, medicinesand pesticides; the sulfoxide chloride is used as a chlorinating agent for synthesis or replacement of organic substances such as alcoholic hydroxyl, acid anhydride, organic sulfonic acid and a nitrocompound; and by the preparation method, the purposes of simple operation, high yield and relatively low cost are achieved.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical intermediates, in particular to a preparation method of N-(4-aminobenzoyl)-L-glutamic acid. Background technique [0002] N-(4-aminobenzoyl)-L-glutamic acid is a pharmaceutical intermediate, mainly used in the production and biochemical research of methotrexate and folic acid, and methotrexate is an antifolate antineoplastic drug , the product is orange-yellow crystalline powder, which mainly hinders the synthesis of tumor cells by inhibiting dihydrofolate reductase, and inhibits the growth and reproduction of tumor cells. It is mainly suitable for choriocarcinoma, malignant hydatidiform mole and various Acute leukemia, almost insoluble in water, ethanol, chloroform and ether, easily soluble in dilute alkali solution, soluble in dilute hydrochloric acid, tetrahydrofolate is an important coenzyme for the synthesis of purine nucleotides and pyrimidine deoxynucleotides in the body, As a folat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C237/36
CPCC07B2200/07C07C201/12C07C231/02C07C231/12C07C237/36C07C233/65C07C205/57
Inventor 张敏华蒋信义徐军徐萌周宇
Owner ABA CHEM SHANGHAI
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