Method for preparing deuterated amino-acid esters by photocatalysis

Abstract

The invention discloses a method for preparing deuterated amino-acid esters by photocatalysis, which is characterized in that in deuterium water which is cheapest and easy to obtain, amino-acid esters are taken as a raw material, and direct deuteration of the amino-acid esters is realized under mild conditions by synergistic catalysis of a plurality of catalysts, so that a target product, namely a deuterated amino-acid ester compound, is obtained. The invention provides a preparation method of deuterated amino-acid esters, which is simple to operate, mild, green, cheap and high in deuteration rate.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a novel photocatalytic method for preparing deuterated amino acid esters. Background technique [0002] The isotope of hydrogen (H) deuterium (D or 2 H), also known as deuterium, consists of a proton, a neutron and an electron. The abundance on Earth is 0.015%, mostly deuterium water D 2 O exists in seawater. In chemistry, especially in the field of medicinal chemistry, the research and synthesis of deuterated compounds has become one of the current research hotspots. Compared with C-H bonds, C-D bonds have higher bond energy, so breaking C-D requires more energy than breaking C-H bonds, and the breaking of C-H bonds is the most important step in the metabolic process of drug compounds. Deuterated compounds can reduce the rate of drug metabolism. Compared with ordinary drug molecules, deuterated drug molecules have the following advantages: prolonging the half-l...

AI Technical Summary

Problems solved by technology

At present, the preparation of deuterated amino acids has disadvantages such as cumbersome steps, low deuterated rate, high cost and energy consumption, and uncontrollable sites (J.Biol.Chem, 1937, 120, 531-536; BBA-Gen Subject, 1977, 497, 1-13; Biochim Biophys Acta, 1976, 446, 479-485.)

And / or the preparation of the deuterated amino acid ester of prior art often needs to be prepared in advance to obtain corresponding imidate (CN113214099A, CN114436871A, CN111004076A, CN110885294A etc.) or dehydrogenated amino acid ester (CN113200895A, CN112358412A etc.), subsequently It can only be carried out under the conditions of an expensive reaction system, which greatly restricts its development, and the method of directly using amino acid ester as a raw material to perform deuterium at a specific position has not been reported.

Images