Preparation method of amino-acid ester or deuterated amino-acid ester compound

A technology of ester compounds and amino acid esters, which is applied in the field of preparation of amino acid esters or deuterated amino acid esters, can solve the problems of unsatisfactory application value and market value, complex deuterated amino acid synthesis steps, and immature synthesis technology. Achieve significant social and economic benefits, the preparation method is easy to operate, and the effect of easy large-scale production

Inactive Publication Date: 2022-05-06
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, the synthesis steps of deuterated amino acids are complex or the synthesis conditions are harsh, the synthesis technology is not mature, and it cannot be selectively deuterated
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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  • Preparation method of amino-acid ester or deuterated amino-acid ester compound
  • Preparation method of amino-acid ester or deuterated amino-acid ester compound
  • Preparation method of amino-acid ester or deuterated amino-acid ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] In the glove box, weigh the photosensitizer Ru(bpy) 3 Cl 2 (52mg, 2 mol%), the corresponding imidate 1a (4mmol), add acetonitrile (20.0 mL), water (720mL, 40mmol), phenylsilane (1731mg, 16 mmol) to the reaction tube equipped with a stir bar , put on the stopper and remove from the glove box, place it above a 30w, 460-470nm blue light at a distance of 3cm, and stir the reaction at a speed of 950r / min at room temperature until the reaction material imidate is completely detected by TLC thin layer chromatography disappear, stop stirring, and the reaction ends. Open the stopper and concentrate under reduced pressure using a rotary evaporator to remove volatile solvents, perform silica gel column chromatography, and concentrate under reduced pressure to obtain amino acid ester compounds with the structural formula (2a). White solid. Yield: 49.2 mg(90%), m.p. 105-107℃. 1 H NMR (400 MHz, Chloroform- d ) δ 7.54 – 7.47 (m, 2H),7.41 – 7.31 (m, 3H), 6.77 – 6.70 (m,...

Embodiment 2

[0060]

[0061] In the glove box, weigh the photosensitizer Ru(bpy) 3 Cl 2 (1.3mg, 1 mol%), the corresponding imidate 1c (0.2mmol), add acetonitrile (1.0mL), water (29mL, 1.6 mmol), phenylsilane (43.3mg, 0.4 mmol) to a stirring bar Put the stopper in the reaction tube, remove it from the glove box, place it above a 30w, 460-470 nm blue light at a distance of 3 cm, and stir the reaction at a speed of 900 r / min at room temperature until TLC thin-layer chromatography detects that the reaction raw material is sub- Amino acid ester disappears completely, stop stirring, and reaction finishes. Open the plug and use a rotary evaporator to remove volatile solvents under reduced pressure, perform silica gel column chromatography, and concentrate under reduced pressure to obtain amino acid ester compounds with the structural formula (2c). White solid. Yield: 63.3 mg (95%), m.p. 105-107℃. 1 H NMR (400 MHz, Chloroform- d ) δ 7.51 –7.47 (m, 2H), 7.39 – 7.30 (m, 3H), 5.80 (s, 2H), 5.0...

Embodiment 3

[0065]

[0066] In the glove box, weigh the photosensitizer Ru(bpy) 3 Cl 2 (2.6mg, 2 mol%), the corresponding imidate 1f (0.2mmol), add acetonitrile (1.0mL), water (29mL, 1.6 mmol), phenylsilane (43.3mg, 0.4mmol) to a stirring bar Put the stopper in the reaction tube, remove it from the glove box, place it above a 30w, 460-470 nm blue light at a distance of 3 cm, and stir the reaction at a speed of 950 r / min at room temperature until TLC thin-layer chromatography detects that the reaction material is sub- Amino acid ester disappears completely, stop stirring, and reaction finishes. Open the stopper and use a rotary evaporator to remove volatile solvents under reduced pressure, perform neutral alumina chromatography, and concentrate under reduced pressure to obtain the deuterated amino acid ester compound with the structural formula (2f). White solid. Yield: 50.9 mg (86%), m.p. 115-117℃. 1 H NMR (400 MHz, Chloroform- d ) δ 7.53(d, J = 7.5 Hz, 2H), 7.36 (dt, J = 13.7,...

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Abstract

The invention discloses a preparation method of an amino-acid ester or deuterated amino-acid ester compound, which comprises the following steps of: adding a photosensitizer and an organic solvent into a reaction container by taking imidic ester, silane and water or heavy water as initial raw materials, carrying out stirring reaction under the irradiation of blue light, detecting that the reaction raw material imidic ester completely disappears by TLC thin-layer chromatography, and filtering to obtain the deuterated amino-acid ester compound. And stopping stirring, removing the volatile solvent, carrying out silica gel column chromatography or neutral alumina column chromatography, and carrying out vacuum concentration to obtain the target amino-acid ester or deuterated amino-acid ester compound. According to the method, blue light catalysis is used for replacing traditional precious metal catalysis, silane and water are used for replacing a traditional hydrogen source for the first time, transfer hydrogenation of the imidic ester compounds is achieved, cheap deuterium water is used as a deuterium source, a series of deuterated amino-acid ester compounds can be prepared, and therefore the production cost is greatly reduced; the method provided by the invention has the advantages of mild catalytic conditions, simple catalytic system, high reaction selectivity, high safety and high synthesis efficiency, and is worthy of popularization and application.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of amino acid ester or deuterated amino acid ester 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 play an indispensable role in life activities. For the human body, amino acids play a very important role: the digestion and absorption of protein in the body is accomplished through amino acids; it plays a role in nitrogen balance; it participates in the formation of enzymes, hormones, and some vitamins. 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 and so on. Therefore, the synthesis of amino acids has great application value and prospect. [0003] At present, there are many researches and repor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C227/40C07C229/36C07B59/00
CPCC07C227/18C07C227/40C07B59/001C07C2601/14C07B2200/05C07C229/36
Inventor 陈景超樊保敏周永云徐建斌和振秀樊瑞峰孙蔚青吴伟
Owner YUNNAN MINZU UNIV
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