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Method for synthesizing alpha-amino-acid ester

An amino acid ester, ketoester technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems affecting the application of imine hydrogenation reaction, and achieve the expansion of substrate application scope, large industrialization potential, The effect of mild reaction conditions

Inactive Publication Date: 2012-09-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, one of the most direct methods for preparing α-amino acids in organic synthesis is the catalytic hydrogenation of imines, but the introduction of metals and hydrogen, high temperature, high pressure and other conditions affect the industrial application of imine hydrogenation reactions

Method used

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  • Method for synthesizing alpha-amino-acid ester
  • Method for synthesizing alpha-amino-acid ester
  • Method for synthesizing alpha-amino-acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Embodiment 1, synthetic 2-amino-tert-butyl phenylacetate

[0070] For the synthetic route map, see figure 2 .

[0071]

[0072] Formula Ⅴ-a Formula IX-a Formula Ⅱ-a

[0073] 1) Add tert-butyl benzoate (0.60mmol, 0.124g), 2-hydroxybenzylamine (1.20mmol, 0.148g), triethylamine (0.12mmol, 0.012g) and 3.0mL methanol to the reactor in sequence. Put the reactor into an oil bath at 60°C, and after reacting for 24 hours, take the reactor out from the oil bath, and spin dry the solvent methanol to obtain the transamination crude product shown in formula IX-a, with a conversion rate of 100 as determined by NMR. %, without further purification, the next reaction was carried out directly.

[0074] 2) Dissolve the transamination crude product obtained from the above reaction in a mixed solution of 12.0 mL tetrahydrofuran and 1 mol / liter hydrochloric acid aqueous solution (the volume ratio of tetrahydrofuran to hydrochloric acid aqueous solution is 1:1), and the temperature of...

Embodiment 2

[0077] Embodiment 2, synthetic 2-amino-tert-butyl phenylacetate

[0078] For the synthetic route map, see image 3 .

[0079]

[0080] Formula Ⅴ-a Formula Ⅹ-a Formula Ⅱ-a

[0081] 1) Add tert-butyl benzoate (0.30mmol, 0.062g), pyridoxamine (0.36mmol, 0.061g), triethylamine (0.06mmol, 0.006g) and 1.5mL methanol to the reactor in sequence. Put the reactor into an oil bath at 60°C, and after reacting for 6 hours, take the reactor out from the oil bath, and spin dry the solvent methanol to obtain the transamination crude product shown in formula Ⅹ-a, and the conversion rate as determined by NMR is 100 %, without further purification, the next reaction was carried out directly.

[0082] 2) Dissolve the transaminated crude product obtained in the above reaction in a mixed solution of 6.0mL tetrahydrofuran and 1 mol / liter hydrochloric acid aqueous solution (the volume ratio of tetrahydrofuran to hydrochloric acid aqueous solution is 1:1), and the temperature of the mixture is a...

Embodiment 3

[0085] Embodiment 3, synthesis 2-amino-2-cyclohexyl-tert-butyl acetate

[0086] For the synthetic route map, see Figure 4 .

[0087]

[0088] Formula Ⅳ-a Formula Ⅺ-a Formula Ⅰ-a

[0089] 1) Add tert-butyl cyclohexyl ketoate (0.60mmol, 0.127g), 2-hydroxybenzylamine (1.20mmol, 0.148g), triethylamine (0.12mmol, 0.012g) and 3.0mL methanol to the reactor in sequence . Put the reactor in an oil bath at 60°C, take it out from the oil bath after reacting for 48 hours, and spin dry the solvent methanol to obtain the transamination crude product shown in formula Ⅺ-a, which can be directly processed without further purification Next reaction.

[0090] 2) Dissolve the transamination crude product obtained from the above reaction in a mixed solution of 12.0 mL tetrahydrofuran and 1 mol / liter hydrochloric acid aqueous solution (the volume ratio of tetrahydrofuran to hydrochloric acid aqueous solution is 1:1), and the temperature of the mixture is at room temperature under hydrolysi...

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Abstract

The invention discloses a method for efficiently synthesizing alpha-amino-acid ester, which comprises the following steps: by using alpha-eleostearates and benzyl amine as raw materials and triethylamine as a catalyst, ammonifying alpha-eleostearates in different structures by a one-pot method under the action of the catalyst; and carrying out after-treatments, including hydrolysis, extraction, column chromatography and the like, to obtain the alpha-amino-acid ester. The maximum reaction yield is up to 95%. In view of the advantages of wide substrate applicability, mild reaction conditions, simple operation and high yield in the method disclosed by the invention, the invention has certain potential industrial application value.

Description

technical field [0001] The invention relates to a method for synthesizing α-amino acid ester. Background technique [0002] α-amino acid and its derivatives are an important class of compounds in organisms and organic synthesis. They are a basic structural unit of protein and play an important role in the function and metabolism of organisms. In organic synthetic chemistry, α-amino acid and its derivatives, as an important class of synthons, are widely used in various fields of medicine and material synthesis. [0003] The synthesis of α-amino acids in the human body is achieved through the transamination reaction of α-keto acids under the action of the coenzyme vitamin B6. This transamination process requires specific biological transaminase catalysis. [0004] At present, one of the most direct methods for preparing α-amino acids in organic synthesis is the catalytic hydrogenation of imines, but the introduction of metals and hydrogen, high temperature, high pressure an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/36C07C229/08C07C229/28C07C227/04C07C227/18C07C255/28C07D333/24
Inventor 史一安薛发珍肖晓
Owner INST OF CHEM CHINESE ACAD OF SCI
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