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Preparation method of N-alkyloxy oxalyl alanine alkyl ester

A technology of alkoxy oxalylalanine alkyl ester and oxalyl alanate, which is applied to the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., which can solve the problem of energy consumption and unsuitability for industrialization Production, expensive and other issues, to achieve the effect of low total cost, large-scale industrial production and high total yield

Active Publication Date: 2013-11-06
SHANGHAI HEGNO PHARMA HLDG +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In the above method, some raw materials are expensive, such as alkoxy oxalyl chloride as a raw material, which is not suitable for industrial production; some reaction times are too long, such as the direct ester acylation of alanine, and the water separation time of the ester acylation reaction is as long as hundreds of years. hours, a large amount of energy is consumed in the process

Method used

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  • Preparation method of N-alkyloxy oxalyl alanine alkyl ester
  • Preparation method of N-alkyloxy oxalyl alanine alkyl ester

Examples

Experimental program
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Effect test

Embodiment 1

[0032] Under nitrogen protection, add 5.81g (50mmol) of ethyl pyruvate, 5.85g (50mmol) of ethyl oxamate, 100mL of 1,2-dichloroethane and 1g (16.65mmol) of acetic acid to the reaction flask at room temperature, and stir at room temperature overnight.

[0033] The next day, 14 g of sodium triacetoxyborohydride (66.06 mmol) was added to the reaction solution, and stirring was continued for 3 hours.

[0034] Add dilute sodium carbonate solution under ice bath to adjust pH=7-8, let stand to separate layers, wash the organic layer with water 30mL*3; concentrate the organic layer to obtain 10.7g of light yellow slurry; pump vacuum distillation, distill off 150 The fraction below °C yielded 10.43 g (48.02 mmol) of the target product with a GC purity of 99.13% and a yield of 96.03%.

Embodiment 2

[0036] Under nitrogen protection, add 5.81g (50mmol) of ethyl pyruvate (50mmol), 5.85g (50mmol) of ethyl oxamate, 0.5g of p-toluenesulfonic acid (2.90mmol) and 100mL absolute ethanol to the reaction flask at room temperature, and stir at room temperature overnight.

[0037] The next day, 0.1 g of palladium carbon was added, and hydrogen gas was passed through the reaction solution at room temperature for 3 hours.

[0038] Filter the reaction solution, concentrate to dry ethanol, add 100mL of petroleum ether, separate layers, wash the organic layer with 30mL*3 of water; concentrate the organic layer to obtain 10.9g of light yellow syrup; 9.11 g (41.94 mmol) of the target product was obtained, the GC purity was 99.35%, and the yield was 83.88%.

Embodiment 3

[0040] Under nitrogen protection, 5.81 g (50 mmol) of ethyl pyruvate, 5.85 g (50 mmol) of ethyl oxalate, 0.5 g of p-toluenesulfonic acid (2.90 mmol), and 0.05 g of 10% palladium carbon were added to the autoclave at room temperature and 100 mL of absolute ethanol, and stirred overnight at room temperature.

[0041] The nitrogen gas was removed, the hydrogen gas was passed through, and the pressure was maintained at 1Mpa, and the reaction was stirred for 2 hours.

[0042] Replace with nitrogen, filter the reaction solution, then concentrate dry ethanol, add 100mL petroleum ether, separate layers, wash the organic layer with water 30mL*3; concentrate the organic layer to obtain 10.7g of light yellow slurry; The fraction below °C yielded 9.98 g (45.94 mmol) of the target product with a GC purity of 99.16% and a yield of 91.89%.

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Abstract

The invention discloses a preparation method of N-alkyloxy oxalyl alanine alkyl ester, comprising the steps of: subjecting pyruvic acid alkyl ester (2) and oxamic acid alkyl ester (3) to a reductive amination reaction so as to obtain a target compound (1) directly in the following reaction route; or, conducting a dehydration reaction to pyruvic acid alkyl ester (2) and oxamic acid alkyl ester (3) first so as to obtain an intermediate Schiff base (4), which then undergoes a reduction reaction, thus obtaining the target compound (1), with a following reaction route; wherein, R1 and R2 respectively represent methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or t butyl. With the advantages of simple operation, short preparation period, low energy consumption, strong industrial feasibility and the like, the preparation method provided in the invention can satisfy the requirements for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of N-alkoxy oxalylalanine alkyl ester, which belongs to the technical field of organic chemical synthesis. Background technique [0002] N-alkoxy oxalylalanine alkyl ester is an important intermediate in the synthesis of vitamin B6. According to the record of existing literature, the preparation of N-alkoxy oxalylalanine alkyl ester has the following methods at present: (1) alanine alkyl ester directly or its hydrochloride and alkoxy oxalyl chloride or oxalic acid Dialkyl ester reacts (FR1533817 in the presence of organic base in methylene chloride; JP43010614 (1968); Bull.Chem.Soc.Japan 42 (5), 1435-1457 (1969); CN91103013, J.Heterocyclic.Chem ., 32,1693-1702(1995); CN200680053471, Bioorg.&Med.Chem.Lett.17(6), 1671-1679(2007)); (2) reaction of alanine and oxalic acid in methanol or ethanol (US3646061 ; JP46002969(1971); Bull.Chem.Soc.Japan 45,1917-1918(1972)); (3) with ethanol as solvent, alanine and oxa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/74C07C231/02
Inventor 刘德铭鲁向阳闫静
Owner SHANGHAI HEGNO PHARMA HLDG
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