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Method for preparing deuterated amino-acid ester by taking heavy water as deuterium source

A technology of amino acid ester and heavy water, applied in the field of chemistry, can solve problems such as complex synthesis conditions, harshness, failure to meet application value and market value, and achieve the effect of simple operation

Inactive Publication Date: 2020-04-14
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, the synthesis of deuterated amino acids is not well developed, the synthesis steps are complex or the synthesis conditions are harsh, and selective deuteration is not possible (J.Biol.Chem, 1937,120,531-536; BBA-Gen Subject, 1977,497,1 -13; Biochim Biophys Acta, 1976, 446, 479-485.)
Therefore, the synthesis of traditional deuterated amino acids has been unable to meet its huge application value and market value

Method used

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  • Method for preparing deuterated amino-acid ester by taking heavy water as deuterium source
  • Method for preparing deuterated amino-acid ester by taking heavy water as deuterium source
  • Method for preparing deuterated amino-acid ester by taking heavy water as deuterium source

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] HB(C 6 f 5 ) 2 (0.002mmol), Zn (0.6mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2ml THF (tetrahydrofuran) was added, and heavy water (0.2mmol) was added and sent out of the glove box. Reaction in 60°C oil bath, TLC monitoring and I 2 The reaction was detected by color development. 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 a deuterium incorporation rate of 97%.

[0037] 1 H NMR (400MHz, CDCl 3 ):δ7.49-7.44(m,2H),7.38-7.29(m,3H),6.74-6.71(m,2H),6.55-6.51(m,2H),5.01(s,0.03H),4.66( s, 1H), 3.71 (d, J=7.16Hz, 6H).

Embodiment 2

[0039]

[0040] In a water-free and oxygen-free glove box under an argon atmosphere, the BF 3 (0.02mmol), Mn (1.0mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2ml 1,4-Dioxane (dioxane) was added, and heavy water (0.5mmol) was added Send out the glove box. Reaction in 110°C oil bath, TLC monitoring and I 2The reaction was detected by color development. 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 95% and a deuterium incorporation rate of 98%.

[0041] 1 H NMR (400MHz, CDCl 3 ):δ7.48-7.45(m,2H),7.38-7.29(m,3H),7.07-7.03(m,2H),6.48-6.44(m,2H),5.02(s,0.02H),4.99( s,1H), 3.73(s,3H).

Embodiment 3

[0043]

[0044] In a water-free and oxygen-free glove box under an argon atmosphere, the ZnI 2 (0.2mmol), Fe (0.1mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2ml tetrahydropyran was added, and heavy water (1.0mmol) was added and sent out of the glove box. Reaction in 70°C oil bath, TLC monitoring and I 2 The reaction was detected by color development. After the reaction was completed, it was concentrated and passed through a column with silica gel to obtain a yellow oily liquid with a yield of 98% and a deuterium incorporation rate of 96%.

[0045] 1 H NMR (400MHz, CDCl 3 ):δ7.49-7.47(m,2H),7.37-7.22(m,3H),6.45(d,J=0.8Hz,1H),6.29-6.24(m,2H),5.10(s,1H), 5.03 (s, 0.04H), 3.85 (s, 3H), 3.70 (d, J=5.8Hz, 6H).

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Abstract

The invention discloses a method for preparing deuterated amino-acid ester by taking heavy water as a deuterium source. According to the method, an imino acid ester compound and heavy water are takenas reaction raw materials, Lewis acid is taken as a catalyst, the target deuterated amino acid ester compound is synthesized through reaction in an organic solvent under the action of a reducing agent, and a reaction formula is shown in the specification, in the formula, R1 and R3 are aryl, and R2 is alkyl. The invention provides the preparation method of the deuterated amino-acid ester. The preparation method is simple to operate, is mild, efficient, and green, and has a high level of deuterium doping.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a method for preparing deuterated amino acid esters by using heavy water as a deuterium source. 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-deuterated exchange, direct deuterated and dehalogenated deuterated methods (J.Am.Chem.Soc.2019, 141, 1467-1472; J.Am.Chem.Soc. 2018, 140, 10970-10974; Adv. Synth. Catal. 2018, 360, 637-641.). 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B59/00C07C227/04C07C229/36C07D333/24
CPCC07B59/001C07B59/002C07C227/04C07D333/24C07B2200/05C07C229/36
Inventor 樊保敏陈景超周永云和振秀樊瑞峰孙蔚青沈国礼
Owner YUNNAN MINZU UNIV
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