Preparation method of N-p-aminobenzoyl-L-glutamic acid

A technology of p-aminobenzoyl and p-nitrobenzoic acid, which is applied in the field of preparation of N-p-aminobenzoyl-L-glutamic acid, can solve the problems such as purity less than 99.9%, and achieve low production cost, The effect of high reaction yield and low environmental pollution

Active Publication Date: 2018-06-12
江苏尚莱特医药化工材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this method is that the purity...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0017] The preparation method of the N-p-aminobenzoyl-L-glutamic acid of the present embodiment has the following steps:

[0018] ①Add 16.7g of p-nitrobenzoic acid (0.1mol), 55mL of tetrahydrofuran and 5mL of DMF to the reaction device, stir and raise the temperature to 55±1°C, slowly add 25.4g of oxalyl chloride (0.2mol) dropwise, dropwise The temperature was raised to reflux, and the reaction was complete.

[0019] After the reaction, cool down to room temperature (20±5°C, the same below), and obtain a solution containing p-nitrobenzoyl chloride for use.

[0020] ②Add 75g of water and 16.9g of sodium glutamate (0.1mol) to the reaction device, adjust the pH value to 8 with 1mol / L sodium hydroxide aqueous solution under stirring, then cool down to 5±1°C, and slowly add For the solution containing p-nitrobenzoyl chloride obtained in step ①, keep the pH = 8 during the dropwise addition, and keep it warm at 5±1°C until the reaction is complete.

[0021] After the reaction was f...

Embodiment 2～ Embodiment 5）

[0025] The preparation method of each embodiment is basically the same as that of Example 1, and the differences are shown in Table 1.

[0026] Table 1

[0027]

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PUM

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Abstract

The invention discloses a preparation method of N-p-aminobenzoyl-L-glutamic acid. The preparation method comprises the following steps of: (1) adopting p-nitrobenzoic acid as a starting material, adopting oxalyl chloride as an acylating chlorination reagent, adopting tetrahydrofuran and DMF (Dimethyl Formamide) as a mixed solvent, and carrying out acylating chlorination reaction to prepare paranitrobenzoyl chloride; (2) carrying out condensation reaction of the paranitrobenzoyl chloride prepared in the step (1) and sodium glutamate to prepare N-p-nitrobenzoyl-L-glutamic acid; (3) adopting hydrazine hydrate as a reducing agent, adopting ferric trichloride hexahydrate as a catalyst, and carrying out reducing reaction of the N-p-nitrobenzoyl-L-glutamic acid prepared in the step (2) to preparethe N-p-aminobenzoyl-L-glutamic acid. The preparation method disclosed by the invention has the beneficial effects that the acylating chlorination reaction selects the oxalyl chloride as the acylating chlorination reagent in the mixed solvent of the tetrahydrofuran and the DMF, the reducing reaction selects the hydrazine hydrate as the reducing agent and selects the ferric trichloride hexahydrateas the catalyst, and finally the N-p-aminobenzoyl-L-glutamic acid with the purity being more than or equal to 99.9% can be obtained.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and in particular relates to a preparation method of N-p-aminobenzoyl-L-glutamic acid. Background technique [0002] N-p-aminobenzoyl-L-glutamic acid is an intermediate in the synthesis of anti-anemia drug folic acid, and its structure is as follows: [0003] . [0004] Chinese patent literature CN105439895A discloses a preparation method of N-p-aminobenzoyl-L-glutamic acid, which uses p-nitrobenzoic acid as a starting material, and first prepares p-nitrobenzoyl chloride through acid chloride reaction , and then make N-p-nitrobenzoyl-L-glutamic acid through condensation reaction with sodium glutamate, and finally get N-p-aminobenzoyl-L-glutamic acid through reduction reaction. The deficiency of this method is: the purity of N-p-aminobenzoyl-L-glutamic acid is less than 99.9%. Contents of the invention [0005] The purpose of the present invention is to solve the above problems, and ...

Claims

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Application Information

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IPC IPC(8): C07C237/36C07C231/12C07C231/02C07C233/83C07C201/12C07C205/57
CPCC07C201/12C07C231/02C07C231/12C07C205/57C07C233/83C07C237/36
Inventor 胡国宜胡锦平李喜龙郑奎奚小金
Owner 江苏尚莱特医药化工材料有限公司
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