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Production technology of N,N-bis(carboxymethyl)-L-lysine

A production process and lysine technology, applied in the N field, can solve problems such as being unfavorable for industrial production, increasing the amount of bromoacetic acid used, reducing product yield, etc., and achieving mild reaction conditions, improving purity, and high purity.

Pending Publication Date: 2018-09-28
CHENGDU AF BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bromoacetic acid is easy to decompose under strong alkali conditions. Adding bromoacetic acid to the strong alkali solution first will increase the amount of bromoacetic acid used, reduce the yield of the product, and increase the cost
This method will further reduce the yield in the scale-up production process and generate a lot of waste, which is not conducive to industrial production

Method used

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  • Production technology of N,N-bis(carboxymethyl)-L-lysine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of N, the production technology of N-bis(carboxymethyl)-L-lysine provided by the present invention adopts the following steps to prepare N,N-bis(carboxymethyl)-L-lysine:

[0037]Step A: prepare 160kg of 7% aqueous sodium hydroxide solution with deionized water, cool down to 5°C, weigh 28kg (100mol) of N6-Cbz-L-lysine and add it to the aqueous sodium hydroxide solution, stir to make N6-Cbz-L-Lysine is completely dissolved, keep adding bromoacetic acid 34.5kg (250mol) in batches at 5°C, then add 160kg of 10% sodium hydroxide aqueous solution dropwise, keep the pH value in the system not lower than 9, After the addition, the temperature was naturally raised to room temperature, and stirring was continued for 1 h to completely dissolve the bromoacetic acid. Slowly raise the temperature to 40°C and stir the reaction for 12h, and the reaction of the system is completed.

[0038] Step B: Cool down the system after the reaction to 0°C, then add 5% hydrochloric acid to a...

Embodiment 2

[0042] A kind of N, the production technology of N-bis(carboxymethyl)-L-lysine provided by the present invention adopts the following steps to prepare N,N-bis(carboxymethyl)-L-lysine:

[0043] Step A: Prepare 350kg potassium carbonate aqueous solution with 50kg potassium carbonate, after cooling to room temperature, weigh 28kg (100mol) of N6-Cbz-L-lysine and add, stir, make N6-Cbz-L-lysine completely Dissolve, slowly add 35 kg (253 mol) of bromoacetic acid at room temperature, stir, keep the pH value in the system not lower than 9, naturally warm up to room temperature, and continue stirring for 0.5 h to completely dissolve the bromoacetic acid. Slowly raise the temperature to 60° C. and stir for 8 hours, and the reaction of the system is completed.

[0044] Step B: Cool down the system after the reaction to 0°C, then add 10% hydrochloric acid to adjust the pH value of the system to 1-2, a large amount of white solids are precipitated, centrifuge after the crystallization is c...

Embodiment 3

[0048] A kind of N, the production technology of N-bis(carboxymethyl)-L-lysine provided by the present invention adopts the following steps to prepare N,N-bis(carboxymethyl)-L-lysine:

[0049] Step A: Prepare 160kg of 7% potassium hydroxide aqueous solution with deionized water, cool down to 5°C, weigh 28kg (100mol) of N6-Cbz-L-lysine and add, stir to make N6-Cbz-L -Lysine is completely dissolved, keep adding 34.5kg (250mol) of bromoacetic acid in batches at 5°C, then add 160kg of 10% aqueous sodium hydroxide solution dropwise, keep the pH value in the system not lower than 9, and naturally heat up to Continue to stir at room temperature for 1 h to completely dissolve the bromoacetic acid. Slowly raise the temperature to 80°C and stir the reaction for 6h, and the reaction of the system is completed.

[0050] Step B: Cool down the system after the reaction to 0°C, then add 10% hydrochloric acid to adjust the pH value of the system to 1-2, a large amount of white solids are pre...

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Abstract

The invention discloses a production technology of N,N-bis(carboxymethyl)-L-lysine, comprising the following steps: Step A: adding N6-Cbz-L-lysine and bromoacetic acid into a dilute solution of inorganic base, keeping the condition of pH value being greater than 9, heating and reacting for 6-12 h; Step B: filtering, centrifuging and drying to obtain N,N-bis(carboxymethyl)-N6-Cbz-L-lysine; Step C:using palladium carbon as a catalyst and carrying out a hydrogen catalytic reaction; and Step D: separating a solid by recrystallization and drying to obtain N,N-bis(carboxymethyl)-L-lysine. Accordingto the production technology of N,N-bis(carboxymethyl)-L-lysine, trans-feeding is adopted: N6-Cbz-L-lysine is firstly poured into the dilute solution of inorganic base, and then bromoacetic acid is added. Thereby, consumption of bromoacetic acid decomposition is reduced, reaction conditions are milder, yield of the product is increased, and cost is lowered. The product is also extracted by a crystallization process. Purity of the product is raised, and the product with higher purity and lower water content is obtained.

Description

technical field [0001] The invention belongs to the technical field of production of NTA intermediates, in particular to a production process of N, N-bis(carboxymethyl)-L-lysine. Background technique [0002] N, N-bis(carboxymethyl)-L-lysine and its derivatives are the main intermediates of drug carriers and nano-targeting technology, and the main raw materials for the production of NTA. Its downstream products are the current domestic and foreign drug carriers. Research hotspots. [0003] Over the past two decades, significant progress has been made in the development of novel drug delivery systems that carry active molecules through different biological barriers to specific targets via drug carriers. Current R&D focus is on overcoming disadvantages of therapeutic molecules such as: solubility (toxicity and absorption issues), stability (degradation in vivo), pharmacokinetics (rapid metabolism) and / or biodistribution (non-specific distribution) Wait. In addition, due to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/22C07C231/12C07C235/12
CPCC07B2200/07C07C231/12C07C269/06C07C271/22C07C235/12
Inventor 张卓赵林吉张翔洪程悦
Owner CHENGDU AF BIOCHEM