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Method for preparing chiral amino acid ester and chiral deuterated amino acid ester

A technology of chiral amino acid ester and amino acid ester, which is applied in the field of chemistry and chemical synthesis, can solve the problems of harsh synthesis conditions, complex synthesis steps of deuterated amino acids, and difficult preparation, etc., and achieve the effect of simple operation

Inactive Publication Date: 2020-03-17
CHONGQING ACAD OF CHINESE MATERIA MEDICA
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0005] At present, the synthesis steps of deuterated amino acids are complex or the synthesis conditions are harsh, and the synthesis technology is immature and cannot be selectively deuterated (J.Biol.Chem, 1937, 120, 531-536; BBA-Gen Subject, 1977, 497 , 1-13; Biochim Biophys Acta, 1976, 446, 479-485.)
At the same time, there are few reports on the synthesis of chiral deuterated amino acids. In 2012, Takahiko Akiyama reported the asymmetric transfer deuteration reaction (Org. Lett.2012, 14,3312-3315.), obtained chiral deuterated amino acid esters, but the deuterium source used in this reaction is expensive and difficult to prepare, and the reaction atom economy is poor, resulting in a large amount of deuterium source waste
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 chiral amino acid ester and chiral deuterated amino acid ester
  • Method for preparing chiral amino acid ester and chiral deuterated amino acid ester
  • Method for preparing chiral amino acid ester and chiral deuterated amino acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] In a water-free and oxygen-free glove box under an argon atmosphere, the PdCl 2 (0.001mmol), (R)-SDP (0.002mmol), Fe(OTf) 2 (0.002mmol), Mn (0.6mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2mlTHF (tetrahydrofuran) was added, and then water (0.2mmol) was added and sent out of the glove box. The reaction was carried out in an oil bath at 60°C. After the completion of the reaction was monitored by TLC, it was concentrated and subjected to silica gel column chromatography to obtain a white solid. Yield 98%, ee 90%.

[0035] 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,1H),4.66(s ,1H),3.71(d,J=7.16Hz,6H).

[0036]

[0037] In a water-free and oxygen-free glove box under an argon atmosphere, the PdCl 2 (0.001mmol), (R)-SDP (0.002mmol), Fe(OTf) 2 (0.002mmol), Mn (0.6mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2mlTHF (tetrahydrofu...

Embodiment 2

[0040]

[0041] In a water-free and oxygen-free glove box under an argon atmosphere, the PdCl 2 (0.001mmol), (R)-SDP (0.002mmol), Fe(OTf) 2 (0.002mmol), Mn (0.6mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2mlTHF (tetrahydrofuran) was added, and heavy water (0.2mmol) was added and sent out of the glove box. The reaction was carried out in an oil bath at 60°C. After the completion of the reaction was monitored by TLC, it was concentrated and subjected to silica gel column chromatography to obtain a white solid. The yield was 92%, and the ee value was 95%.

[0042] 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,1H),4.99(s ,1H),3.73(s,3H).

[0043]

[0044] In a water-free and oxygen-free glove box under an argon atmosphere, the PdCl 2 (0.001mmol), (R)-SDP (0.002mmol), Fe(OTf) 2 (0.002mmol), Mn (0.6mmol) (0.6mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tub...

Embodiment 3

[0047]

[0048] In a water-free and oxygen-free glove box under an argon atmosphere, the PdCl 2 (0.001mmol), (R)-SDP (0.002mmol), Fe(OTf) 2 (0.002mmol), Mn (0.6mmol) and imidate (0.2mmol) were sequentially added to a 10mL reaction tube, then 2mlTHF (tetrahydrofuran) was added, and heavy water (0.2mmol) was added and sent out of the glove box. The reaction was carried out in an oil bath at 60°C. After the completion of the reaction was monitored by TLC, it was concentrated and subjected to silica gel column chromatography to obtain a white solid. The yield was 94%, and the ee value was 90%.

[0049] 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,1H),3.85(s,3H),3.70(d,J=5.8Hz,6H).

[0050]

[0051] In a water-free and oxygen-free glove box under an argon atmosphere, the PdCl 2 (0.001mmol), (R)-SDP (0.002mmol), Fe(OTf) 2 (0.002mmol), Mn (0.6mmol) (0.6mmol) and imidate (0.2mmol) were sequentially added...

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Abstract

A method for efficiently preparing chiral amino acid ester and chiral deuterated amino acid ester is disclosed. Water or deuterated water is adopted as a hydrogen source or a deuterium source to achieve asymmetric transfer hydrogenation or deuteration of imino acid ester in an inert gas atmosphere to obtain the chiral amino acid ester and chiral deuterated amino acid ester derivatives. The methodfor preparing the chiral amino acid ester and chiral deuterated amino acid ester, which is simple and convenient to operate, mild, efficient and green, is provided.

Description

technical field [0001] The invention belongs to the technical field of chemistry, further belongs to the technical field of chemical synthesis, and specifically relates to a preparation method of chiral amino acid ester and chiral deuterated amino acid ester organic compound. Background technique [0002] Amino acid is a general term for a class of organic compounds containing amino and carboxyl groups in the molecule. Amino acids are a very useful class of compounds. For the human body, amino acids play a very important role: 1. The digestion and absorption of protein in the body is accomplished through amino acids; 2. Play a role in nitrogen balance; 3. Transform into sugar or fat; 4. Participate in the formation of enzymes, hormones, some vitamins, etc. Similarly, amino acid also plays a very important role in industrial production and human life, and it plays an irreplaceable role in medical health, material base, food, etc. In synthetic chemistry, amino acids also pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/06C07C229/36C07B59/00
CPCC07C227/06C07B59/001C07B2200/07C07B2200/05C07C229/36
Inventor 樊保敏杨大坚詹永罗杨李娟陈景超周永云沈国礼
Owner CHONGQING ACAD OF CHINESE MATERIA MEDICA
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