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Preparation method of chiral deuterated amino acid ester compound
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A technology of ester compounds and amino acid esters, which is applied in the field of preparation of chiral deuterated amino acid ester compounds, can solve the problems of harsh synthesis conditions, complex synthesis steps, deuteration, etc., and achieve high synthesis efficiency, simple preparation method, and reaction The effect of mild conditions
Active Publication Date: 2021-02-12
YUNNAN MINZU UNIV
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[0004] At present, the synthesis of deuterated amino acids is not well developed, the synthesis steps are complicated or the synthesis conditions are harsh, and at the same time, selective deuteration is not possible
Therefore, the synthesis of traditional deuterated amino acids has been unable to meet its huge application value and market value
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[0037] The preparation method of the chiral deuterated amino acid of the present invention is to obtain the chiral deuterated amino acid by deprotecting the target chiral deuterated amino acid ester compound, and the general reaction formula is as follows:
[0038]
[0039] The present invention will be further described below with specific implementation case:
Embodiment 1
[0041]
[0042] (R,R)-QuinoxP*(0.012mmol), RhCl 3 (0.005mmol) into the reaction tube in turn, then add 1ml 1,2-dichloroethane and stir for 30min, then add Cu(OTf) 2 (coppertrifluoromethanesulfonate) (0.02mmol) stirred for 10min, then added 0.6mmol of zincpowder, then added 0.2mmol of dehydroamino acid ester, then added 1ml of 1,2-dichloroethane, took out the glove box and added 40 μl Heavy water, reacted in an oil bath at 70°C, monitored by TLC and detected by liquid mass method. After the reaction was completed, concentrated, and passed through a column with silica gel to obtain a white solid with a yield of 98% and an ee value of 93%. According to the 1H NMR spectrum ( figure 1) to calculate the deuterium incorporation rate of the compound to be 78%.
[0046] (R,R)-QuinoxP*(0.012mmol), RhCl 3 (0.005mmol) into the reaction tube in turn, then add 1ml 1,2-dichloroethane ring and stir for 30min, then add Zn(OTf) 2 (Zinctrifluoromethanesulfonate) (0.02mmol) stirred for 10min, then added zincpowder 0.6mmol, then added dehydroamino acid ester 0.2mmol, then added 1ml 1,2-dichloroethane, took out the glove box and added 40 μl Heavy water, reacted in an oil bath at 70°C, monitored by TLC and detected by liquid-mass method. After the reaction was completed, it was concentrated and passed through a column with silica gel to obtain a white solid with a yield of 98% and an ee value of 91%. According to the 1H NMR spectrum ( figure 2 ) to calculate the deuterium incorporation rate of the compound to be 77%.
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Abstract
The invention discloses a preparation method of a chiral deuterated amino-acid ester compound, which comprises the following steps: by using a dehydroamino-acid ester compound and heavy water as reaction raw materials, adding a ligand, a catalyst and a reducing agent into an organic solvent environment under inert gas atmosphere conditions to react to synthesize the chiral deuterated amino-acid ester compound. The catalyst comprises transition metal and Lewis acid, and the reaction general formula of the catalyst is as follows: in the formula, R1 is selected from aryl or alkyl. The invention provides a novel method for preparing a chiral deuterated amino acid compound, which comprises the following steps: in an organic solventsystem, carrying out transfer deuteration on dehydroamino acidester by using heavy water as a deuterium source in an inert gas atmosphere to obtain a chiral deuterated amino acid ester derivative, and removing a protective group to obtain the chiral deuterated amino acid. The method is simple in operation, mild in reaction condition and high in synthesis efficiency, the yield of the chiral deuterated amino acid compound reaches up to 98%, the deuteriumdoping rate reaches up to 80%, and the method has further application and popularization value.
Description
technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of chiral deuterated amino acid ester compounds. Background technique [0002] Deuterium (D or 2 H) is an isotope of hydrogen (H) with twice the atomic mass of hydrogen, also known as heavy hydrogen. Deuterium, non-toxic, non-radioactive. Deuterated compounds are a very important class of high value-added chemicals. At present, the preparation methods of deuterated compounds mainly include hydrogen-deuterium exchange, direct deuteration and dehalogenated deuteration. In the field of medicinal chemistry, the role of deuterated compounds has become increasingly prominent. When the C-H bond at one or several positions in the drug molecule is replaced by a C-D bond, the selectivity and activity of the drug can still be maintained. Moreover, compared with the C-H bond, the vibration frequency of the C-D bond is lower, the bond energy is...
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