Preparation method of gamma-deuterated amino-acid ester

By reacting deuterated with deuterated reagents under the action of the catalytic system, the existing deuterated amino acid synthesis methods have solved the problems of poor universality and poor uniformity of deuterated amino acid synthesis methods, and achieved high selectivity deuterated at the γ-position of amino acids, which are highly efficient, environmentally friendly and low-cost.

CN119707612APending Publication Date: 2025-03-28NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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Patent Information

Application Number
CN202411597401.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-11-11
Publication Date
2025-03-28

AI Technical Summary

Technical Problem

The existing deuterated amino acid synthesis methods are poor in popularity, resulting in a specific synthetic route for each amino acid, which significantly increases the time and cost, and the uniformity of deuteratedness is poor, limiting its application in labeling and tracer experiments.

Method used

A method of preparing γ-deuterated amino acid ester is adopted. Deuterated reaction with deuterated reagent under normal pressure under the action of the catalytic system. Palladium acetate, 2-hydroxynicotinamide and silver trifluoroacetate are used as the catalytic system, and heavy water is used as the deuterium source and solvent to achieve high regioselective deuterated at the γ position of amino acid ester compounds.

Benefits of technology

It achieves high selective deuterated at the γ amino acid position, simple reaction operation, high deuteration and yield, simple separation, low cost, environmentally friendly reagents, and is suitable for the preparation of a variety of amino acid esters.

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Abstract

The invention discloses a preparation method of gamma-deuterated amino-acid ester, which comprises the following steps: by taking an amino-acid ester compound as shown in a formula I as a raw material, carrying out deuteration reaction on the amino-acid ester compound and a deuterium source reagent at normal pressure under the action of a catalytic system, and separating and purifying a reaction product to obtain a gamma-deuterated product; the catalytic system comprises a palladium catalyst, a guiding group and silver salt for maintaining the valence state of metal palladium; and # imgabs0 #. The method can be completed under conventional conditions, the one-pot reaction does not need to replace a solvent halfway, the reaction operability is high, and the deuteration effect is good; the process method is good in universality and can be used for preparing various amino-acid ester compound deuterated products; the method has the characteristics of safety, environmental protection and low cost.
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