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Preparation method of L-2,4-diaminobutyrate hydrochloride

A technology of diaminobutyric acid hydrochloride and aminobutyric acid is applied in the preparation of carbamic acid derivatives, the preparation of organic compounds, the preparation of cyanide reactions, etc., and can solve the problems of large pollution of three wastes, cumbersome operations, and long routes. Achieve the effect of reducing production costs, reducing three waste emissions, and reducing the use of

Active Publication Date: 2019-10-11
CHENGDU BAISHIXING SCI & TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The entire operation process is lengthy, the reaction conditions are harsh, and the cost is high, which is not conducive to production scale-up
[0007] The above several schemes all have the disadvantages of long route, cumbersome operation, large pollution of three wastes and high cost, and are not suitable for production scale-up

Method used

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  • Preparation method of L-2,4-diaminobutyrate hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] S1: Add 14.6 g of L-glutamine (0.1 mol) to a 500 mL three-neck flask, add 150 ml of water, 10 g of sodium hydroxide (0.25 mol), stir and clarify, then add 26.2 g of Boc anhydride (0.12 mol), React overnight at room temperature, and monitor the completion of the reaction by spotting the plate;

[0033] S2: Add 4 grams of sodium hydroxide (0.1 mol), and then add 107 grams of 7% sodium hypochlorite (0.1 mol) dropwise at room temperature. After the addition is completed, the temperature is naturally raised for half an hour, and the reaction is monitored by spotting the plate;

[0034] S3: Lower the reaction solution to room temperature, adjust the pH to 5~6 with concentrated hydrochloric acid, desalt through cationic resin exchange resin, and elute with 5% ammonia water as the eluent. After the eluent is concentrated, adjust the pH with concentrated hydrochloric acid From 2 to 3, beat with ethanol to obtain the crude product of L-2,4-diaminobutyric acid hydrochloride, and d...

Embodiment 2

[0036] S1: Add 43.8 g of L-glutamine (0.3 mol) to a 1000 mL three-necked flask, add 450 ml of water, 30 g of sodium hydroxide (0.25 mol), stir and clarify, then add 78.6 g of Boc anhydride (0.12 mol), React overnight at room temperature, and monitor the completion of the reaction by spotting the plate;

[0037] S2: Add 12 grams of sodium hydroxide (0.1 mol), and then add 321 grams of 7% sodium hypochlorite (0.1 mol) dropwise at room temperature. After the addition is completed, the temperature is raised naturally for half an hour, and the reaction is monitored by spotting the plate;

[0038] S3: The reaction solution is lowered to room temperature, and the pH is adjusted to 5~6 with concentrated hydrochloric acid, desalinated by cationic resin exchange resin, and eluted with 5% ammonia water as the eluent, after the eluent is concentrated, the pH is adjusted with concentrated hydrochloric acid From 2 to 3, beat with ethanol to obtain the crude product of L-2,4-diaminobutyric a...

Embodiment 3

[0040] S1: Add 146 grams of L-glutamine (1 mol) to a 3000 mL three-neck flask, add 1500 milliliters of water, 100 grams of sodium hydroxide (2.5 mol), stir and clarify, then add 262 grams of Boc anhydride (0.12 mol), React overnight at room temperature, and monitor the completion of the reaction by spotting the plate;

[0041] S2: Add 40 grams of sodium hydroxide (1 mol), and then add 1070 grams of 7% sodium hypochlorite (1 mol) dropwise at room temperature. After the addition is completed, the temperature is naturally raised to react for half an hour, and the reaction is monitored by spotting the plate;

[0042] S3: The reaction solution is lowered to room temperature, and the pH is adjusted to 5~6 with concentrated hydrochloric acid, desalinated by cationic resin exchange resin, and eluted with 5% ammonia water as the eluent, after the eluent is concentrated, the pH is adjusted with concentrated hydrochloric acid From 2 to 3, beat with ethanol to obtain the crude product of ...

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Abstract

The invention belongs to the technical field of organic chemistry, and discloses a preparation method of L-2,4-diaminobutyrate hydrochloride. The method includes the following steps that S1, L-glutamine is subjected to Boc protection under an alkaline condition to obtain a N-BOC-L-glutamine aqueous solution; S2, a saturated sodium hypochlorite solution is dropwise added into the N-Boc-L-glutamineaqueous solution obtained in the S1 for a degradation reaction, and a L-2-N-Boc-4-aminobutyric acid crude product solution is obtained; S3, the L-2-N-Boc-4-aminobutyric acid crude product solution iscondensed, the pH is adjusted with 2N hydrochloric acid, salt is removed with cation exchange resin, dilute ammonia water is used as an elution agent for elution, the eluent is condensed, concentratedhydrochloric acid is added for adjusting the pH of a concentrated solution, absolute ethyl alcohol is added, and after crystallization, filtering and drying, the L-2,4-diaminobutyrate hydrochloride is obtained. The method has the advantages that the synthetic route is short, operation is simple, three wastes pollution is less, the yield is high and the cost is low, and the method is an ideal scheme for industrial scale-up production.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of L-2,4-diaminobutyric acid hydrochloride. Background technique [0002] Ectoin is a natural substance and is an exclusive patent of MERCK (Merck) Group. It can prevent UVA-induced photoaging by inhibiting the release of UVA-induced second messengers, and can effectively improve the immune protection of skin cells. Ability to increase cell repair ability, so that the skin can effectively resist the invasion of microorganisms and allergens. Experiments have shown that: Ectoin can resist the damage of ultraviolet rays to the skin and repair the DNA damage of cells caused by ultraviolet rays. Because it can relieve various stresses on the skin: ultraviolet damage, skin aging caused by dry environment, skin deterioration caused by surfactants, etc., Ectoin has cell repair and moisturizing functions, and is used as a cell repair additive to...

Claims

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Application Information

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IPC IPC(8): C07C227/20C07C229/26
CPCC07C269/04C07C269/06C07C227/20C07C271/22C07C229/26
Inventor 石常青
Owner CHENGDU BAISHIXING SCI & TECH IND
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