Preparation method of N-(2-aminoethyl) glycine derivative

A technology for glycine and derivatives, which is applied in the field of preparation of N-glycine derivatives, can solve the problems of difficult tracking, identification and purification, complex operation and purification, and low production yield, and achieve optimal reaction condition parameters, cheap and easy-to-obtain raw materials, and high purity high effect

Active Publication Date: 2021-10-15
成都泰和伟业生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In view of the above-mentioned defects of the prior art, the technical problem to be solved by the present invention is that the existing chemical preparation method of N-(2-aminoethyl)glycine derivatives has complex operation and purification, difficult tracking identification and purification, resulting in low production yield , the defect problem of high product price

Method used

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  • Preparation method of N-(2-aminoethyl) glycine derivative
  • Preparation method of N-(2-aminoethyl) glycine derivative
  • Preparation method of N-(2-aminoethyl) glycine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Embodiment 1, the preparation of formula A compound

[0085] step 1,

[0086] Compound A-1 (1.04g, 10mmol) was added to 20ml of tetrahydrofuran, then sodium bicarbonate (1.6g, 20mmol) and 20ml of water were added, and Cbz-Osu (3g, 12mmmol) was slowly added under stirring for about 30min to maintain the pH ≈8. After the addition, the system was stirred at room temperature until the reaction was complete, concentrated to remove THF, extracted with ethyl acetate, dried and concentrated the organic phase to obtain product A-2 (1.9 g, yield 80%).

[0087] Step 2,

[0088] A solution of A-2 (0.95 g, 4 mmol) in 40 mL of acetone was added to 15 mL of saturated sodium bicarbonate solution. Cool down to below 5°C with an ice bath, add NaBr (0.1g, 1mmol), TEMPO (0.015g, 0.1mmol), then sodium hypochlorite (0.6g, 8.0mmol), sodium chlorate (0.875g, 8.0mmol) in batches Add, keep the system temperature below 5°C, stir until the reaction is complete, add isopropanol and stir for 30 m...

Embodiment 2

[0089] Embodiment 2, the preparation of formula A compound

[0090] step 1,

[0091] Compound A-1 (1.04g, 10mmol) was added to 14ml of tetrahydrofuran, then sodium bicarbonate (1.9g, 25mmol) and 16ml of water were added, and Cbz-Osu (2.9g, 11mmmol) was slowly added under stirring for about 30min, and maintained pH≈8. After the addition, the system was stirred at room temperature until the reaction was complete, concentrated to remove THF, extracted with ethyl acetate, dried and concentrated the organic phase to obtain product A-2 (1.95 g, yield 82%).

[0092] Step 2,

[0093] A solution of A-2 (0.95 g, 4 mmol) in 30 mL of acetone was added to 15 mL of saturated sodium bicarbonate solution. Cool down to below 5°C with an ice bath, add NaBr (0.133g, 133mmol), TEMPO (0.019g, 0.133mmol), then sodium hypochlorite (0.67g, 9.0mmol), sodium chlorate (0.98g, 9.0mmol) in batches Add, keep the system temperature below 5°C, stir until the reaction is complete, add isopropanol and stir ...

Embodiment 3

[0094] Embodiment 3, the preparation of formula A compound

[0095] step 1,

[0096] Compound A-1 (1.04g, 10mmol) was added to 14ml of tetrahydrofuran, then sodium bicarbonate (2.4g, 30mmol) and 21ml of water were added, and Cbz-Osu (3.3g, 15mmmol) was slowly added under stirring for about 30min, and maintained pH≈8. After the addition, the system was stirred at room temperature until the reaction was complete, concentrated to remove THF, extracted with ethyl acetate, dried and concentrated the organic phase to obtain product A-2 (2.01 g, yield 85%).

[0097] Step 2,

[0098]A solution of A-2 (0.95 g, 4 mmol) in 45 mL of acetone was added to 15 mL of saturated sodium bicarbonate solution. Cool down to below 5°C with an ice bath, add NaBr (0.08g, 0.08mmol), TEMPO (0.012g, 0.08mmol), then sodium hypochlorite (0.75g, 10.0mmol), sodium chlorate (1.09g, 10.0mmol) Add in batches, keep the system temperature below 5°C, stir until the reaction is complete, add isopropanol and stir ...

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Abstract

The invention discloses a preparation method of an N-(2-aminoethyl) glycine derivative, which comprises the steps of by taking hydroxyethyl ethylenediamine as a raw material, carrying out Cbz protection reaction of primary amine, and then carrying out oxidation reaction to obtain an N-(2-aminoethyl) glycine derivative product compound. According to the preparation method of the N-(2-aminoethyl) glycine derivative, reaction conditions for obtaining carboxylic acid groups through primary alcohol oxidation are optimized, primary amine protected hydroxyethyl ethylenediamine is subjected to one-step oxidation reaction to directly obtain the N-(2-aminoethyl) glycine derivative product compound, the route is short, the reaction conditions are mild, the safety is good, the purification is easy, and the yield is greatly improved; and the method is mild in condition, good in operation safety, green and environment-friendly in post-treatment, capable of achieving environment-friendly industrial production and wide in application prospect.

Description

technical field [0001] The invention relates to the technical field of synthesis of organic intermediate compounds, more specifically, to a preparation method of N-(2-aminoethyl)glycine derivatives. Background technique [0002] N-(2-aminoethyl)glycine compound contains two amino groups and a carboxylic acid group in its structure, and is a widely used organic compound. The structural formula is as follows: [0003] [0004] N-(2-aminoethyl)glycine is the alignment unit of the peptide nucleic acid backbone. In the field of organic synthesis and pharmaceutical compound synthesis, N-(2-aminoethyl)glycine, as a building block for the synthesis of various pharmaceutical compounds, can introduce amino groups or carboxylic acid groups into the core structure to adjust the water-solubility and fat-solubility of pharmaceutical compounds. Improving the oil-water partition coefficient of pharmaceutical compounds is of great significance in the field of pharmaceutical synthesis. T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/06C07C271/52
CPCC07C269/04C07C269/06C07C271/52Y02P20/55
Inventor 邓一建冯建雍刚邓小艳谭康利
Owner 成都泰和伟业生物科技有限公司
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