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Preparation method of L-penicillamine

A technology of penicillamine and penicillamine hydrochloride, which is applied in the field of medicine and chemical industry, can solve the problems of high price of splitting reagent chloramphenicol, waste of raw materials and energy, manpower, and unsuitability for mass production, and achieve solvent recovery and application Convenient, easy to recycle and apply, low disassembly cost effect

Active Publication Date: 2021-03-16
CHENGDU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has two big defects: the one, the defect of reaction itself: acetyl chloride is big to environmental pollution as racemization reagent, and reaction impurity is many, and product yield is low, and quality is poor
The second is that the splitting reagent chloramphenicol itself is expensive. If it is not recycled, the production cost of the product will increase exponentially, and the recycling will increase the reaction steps, resulting in a great waste of raw materials, energy and manpower, which is not suitable for industrialized mass production.

Method used

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  • Preparation method of L-penicillamine
  • Preparation method of L-penicillamine
  • Preparation method of L-penicillamine

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preparation example Construction

[0041] The preparation method of L-penicillamine of the present invention, the corresponding chemical reaction process is as follows:

[0042]

Embodiment 1

[0044] A method for preparing L-penicillamine, steps S1 to S7 are carried out independently in respective reaction tanks, and intermediate products are separated from the reaction tanks after each step is completed, and then the intermediate products are used in the next step one step. Proceed as follows:

[0045] Synthesis of S1, isopropyl-D-penicillamine

[0046] Add 149.5 grams of D-penicillamine and 450 milliliters of acetone to a 1L three-necked bottle, stir and heat to 55°C, follow the reaction with a thin layer (n-butanol: glacial acetic acid: water volume ratio 4:1:1), 2 After one hour, the reaction was completed, and then concentrated under reduced pressure at room temperature to remove part of the acetone so that the volume of the reaction solution was reduced to one-third of the original volume, cooled to 5°C and stirred for 1 hour, filtered to obtain a white filter cake, dried in the air to obtain a white powder Isopropyl-D-penicillamine, weighing 172.8g, yield: ...

Embodiment 2

[0060] A method for preparing L-penicillamine, steps S1 to S4 are continuously completed in the same reaction tank, and the reaction tank does not need to be replaced midway. Proceed as follows:

[0061] S1. First, add 149.5g of D-penicillamine and 450ml of acetone into reaction tank A, heat to a temperature of 55°C, and track the reaction in a thin layer (n-butanol:glacial acetic acid:water volume ratio 4:1:1), After 2 hours, the reaction was completed, and then, the remaining acetone was removed by evaporation under reduced pressure at room temperature, and isopropyl-D-penicillamine was obtained in the reaction tank.

[0062] S2. Add 517.5ml of ethyl formate directly to the reaction tank of step S1, reflux reaction at a temperature of 53°C, and monitor the reaction with a thin layer (methanol:dichloromethane volume ratio 1:9). After 5 hours, the reaction is complete, and then reduce to normal temperature. The remaining ethyl formate was removed by pressure evaporation, and ...

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Abstract

The invention discloses a preparation method of L-penicillamine, which comprises the following steps: protecting sulfydryl and amino in penicillamine by using acetone and ethyl formate to obtain Nformyl isopropyl penicillamine; then, conducting racemization on N-formyl isopropyl-D-apenem by adopting acetic acid or a mixed solution of acetic acid and methylbenzene to acquire N-formyl isopropyl-D and L-apenem; reacting N-formyl isopropyl-D, Lapenem and hydrochloric acid to prepare N-formyl isopropyl-D, L-apenem hydrochloride; dissociating N-formyl isopropyl-D and Lapenem hydrochloride in lower alcohol through organic alkali to obtain a dissociated racemate D and L-apenem; d, reacting the L-Penicillamine with a resolving agent L-tartaric acid to obtain L-Penicillamine. Ltartrate; carrying outsalt hydrolysis on the L-Penicillamine. L-tartrate by using organic alkali to obtain the L-Penicillamine. According to the preparation method disclosed by the invention, the used resolution reagent is low in price, the reaction condition is mild, the product yield is high, and feasibility is provided for industrial mass production of the L-Penicillamine.

Description

technical field [0001] The invention relates to the technical field of medicine and chemical industry, in particular to a method for preparing L-penicillamine from D-penicillamine as an initial raw material. Background technique [0002] Cyanodamine is an optically active substance with D-type, L-type and D, L-type. D-penicillamine is a colorless powdery crystal with a faint smell of amino sulfur, easily soluble in water, slightly soluble in ethanol, almost insoluble in ether, chloroform, carbon tetrachloride, aliphatic or aromatic hydrocarbons. Initially, the only role of penicillamine was in the total synthesis of penicillin. It was the center of the penicillin structural unit and a key substance that could be used to elucidate the structure of penicillin. By 1956, it was first introduced into medicine as a chelating agent to promote the removal of heavy metals and non-physiological heavy metals (antidote for heavy metal poisoning) above physiological concentrations. Gra...

Claims

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Application Information

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IPC IPC(8): C07C319/28C07C323/58C07C319/02
CPCC07D277/06C07C319/02C07C319/28C07B2200/07C07C323/58
Inventor 贾爱琼赵经伟邓俊丰宋艳霞马晓黎刘潇汪令李直
Owner CHENGDU UNIV
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