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Method for synthesizing N-methyl-D-aspartate

A technology for aspartic acid and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as complex reactions and difficult separation of products, and achieve the effect of easy separation and extraction and simple process

Active Publication Date: 2012-07-04
ANHUI HUAHENG BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The report uses a direct methylation method, there is racemization, and the amino acid needs to be protected, the reaction is complicated, and the product is not easy to separate

Method used

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  • Method for synthesizing N-methyl-D-aspartate

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preparation example Construction

[0009] A kind of synthetic method of N-methyl-D-aspartic acid, comprises the following steps:

[0010] a) in methanol solvent, add D-aspartic acid, paraformaldehyde and reducing agent, carry out reaction;

[0011] b) After the reaction, the white precipitate produced by the reaction is filtered out, and then washed with methanol to obtain the product N-methyl-D-aspartic acid.

[0012] The present invention adopts reductive amination method, one-step reaction to obtain the product, the process is simple, and the product is easy to separate and extract.

[0013] The reaction formula is as follows:

[0014]

[0015] The invention uses D-aspartic acid as raw material, reacts excess paraformaldehyde and reducing agent in methanol solvent. After the reaction, a white precipitate appeared, which was separated and washed with methanol to obtain the product N-methyl-D-aspartic acid.

[0016] The filtrate obtained by filtering and the washing liquid obtained by washing in the step...

Embodiment 1

[0023] 13.3g of D-aspartic acid, 1.995g of paraformaldehyde and 6.65g of sodium cyanoborohydride were respectively added into a three-necked flask containing 133g of methanol solvent, and the reaction was stirred at room temperature at pH 6.0-8.0 for 18 hours. After the reaction was completed, the white precipitate was filtered and washed twice with 20-30ml of methanol to obtain 5.5g of the product. Collect the filtrate and washings, pass through a chromatographic column (φ20×500) equipped with 100g silica gel (200~300 mesh) at a flow rate of 5ml / min, use a chloroform-methanol-water system with a ratio of 6:4:1 300ml was eluted, and the collected eluent was concentrated under reduced pressure to crystallize and then dried to obtain 2.3g of the product, with a total yield of 53%. Product optical rotation: [α]D 20 =-28.32° (c=1,6N HCl), mp 187°C.

Embodiment 2

[0025] 13.3g of D-aspartic acid, 2.97g of paraformaldehyde and 9.5g of sodium cyanoborohydride were respectively added into a three-necked flask filled with 240.3g of methanol solvent, and the reaction was stirred at room temperature at pH 6.0-8.0 for 18 hours. After the reaction was completed, the white precipitate was filtered and washed twice with 20-30ml of methanol to obtain 9.2g of the product. The filtrate and methanol washings were carried out in the same manner as in Example 1 to obtain 3.7 g of the product. The total yield is 87.8%. Product optical rotation: [α]D 20 =-28.85° (c=1,6N HCl), mp 188°C.

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Abstract

The invention mainly aims to provide a method for synthesizing a product which is N-methyl-D-aspartate through one-step reaction. According to the technical scheme, the method comprises the following steps: (a) adding D-aspartate, paraformaldehyde and a reductant into methanol solvent for reaction; and (b) filtering to separate out a white precipitate produced from reaction after the reaction finishes, and washing the white precipitate with methanol to obtain the product which is the N-methyl-D-aspartate. According to the technical scheme of the invention, the method adopts the reductive amination method to synthesize the product through one-step reaction and is simple. The product synthesized by adopting the method is easy to separate and extract.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a method for synthesizing N-methyl-D-aspartic acid. Background technique [0002] N-methyl-D-aspartic acid (NMDA) is a methylation product of D-aspartic acid, and generally exists only in the nervous and endocrine tissues of humans or animals. Many studies have shown that an appropriate amount of NMDA can significantly promote the release of growth hormone, pituitary hormone, gonadotropin and prolactin in the pituitary gland of animals. It is a new type of feed additive with high efficiency and growth promotion. In recent years, with the continuous development of molecular biology and cell biology, and the deepening of the research on its mechanism of action, NMDA, as a new functional food additive, has broad application prospects. [0003] So far, only the journal "Fine and Specialty Chemicals" has reported a synthesis of N-methyl-D-aspartic acid (2011, 19(1): 45-48)....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/24C07C227/18
Inventor 蒋光玉胡杰
Owner ANHUI HUAHENG BIOTECH
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