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Method and product for preparing optically pure n-methyl amino acid ester

A methyl amino acid ester, amino acid ester technology, applied in chemical instruments and methods, cyanide reaction preparation, organic compound preparation and other directions, can solve problems such as incompatibility, and achieve the effects of low cost, high yield and simple operation

Active Publication Date: 2016-09-07
绍兴众昌化工股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that this method is not suitable for amino acids with basic side chains, such as lysine, histidine and tryptophan

Method used

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  • Method and product for preparing optically pure n-methyl amino acid ester
  • Method and product for preparing optically pure n-methyl amino acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A method for preparing optically pure N-methyl amino acid ester, the specific reaction route can be found in the attached figure 1 , 2 , from N-methyl-N-benzyl-amino acid ester to obtain optically pure N-methyl amino acid ester by hydrogenation debenzylation.

[0032] In particular, when N-methyl-N-benzyl-amino acid ester is not an existing product that has been purchased, N-methyl-N-benzyl base - amino acid ester.

[0033] In particular, when N-benzyl-amino acid ester is not a commercially available product, N-benzyl-amino acid ester is obtained by reacting amino acid ester hydrochloride with aromatic aldehyde.

[0034] In particular, when the amino acid ester hydrochloride is not an existing commercially available product, the amino acid ester hydrochloride is obtained from α-amino acid through esterification.

[0035] Further, this embodiment also includes a method of directly obtaining an optically pure N-methyl amino acid ester directly from an α-amino acid, inc...

specific Embodiment

[0045] Step 1) Obtain amino acid ester hydrochloride from α-amino acid through lipidation reaction.

[0046] Specifically, in this example, L-amino acid was used to synthesize L-amino acid methyl ester hydrochloride. The experimental procedure was as follows: add L-amino acid (80 mmol) and methanol 250 mL into a 500 mL three-neck round bottom flask, Mechanically stirred and cooled to 0°C, slowly added thionyl chloride (38.07g, 320mmol) dropwise, after the dropwise addition was completed, the reaction was refluxed for 2h, and the solvent was evaporated to dryness under reduced pressure to obtain the crude product, which was washed with frozen diethyl ether (50mL×3), and the Drying under pressure gave a white solid, ie L-amino acid methyl ester hydrochloride. Among them, hydrogen chloride gas is used in the salt-forming reaction.

[0047] In order to further identify the type of the compound obtained by the above reaction, the L-amino acids used are L-valine, tryptophan, phenylal...

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Abstract

The invention belongs to the field of organic synthesis of amino acids and discloses a method for preparing optically pure N-methyl amino-acid ester. The method comprises the following steps of carrying out esterification reaction on amino acid as a starting raw material and aldehyde to form an imine intermediate, carrying out reductive amination in the presence of palladium carbon, and carrying out hydrogenation and debenzylation to finally synthesize optically pure N-methyl amino-acid ester. The method has the advantages of simplicity in method, mild reaction conditions and good adaptability and side chains of D-type or L-type amino acid do not need to be protected.

Description

technical field [0001] The invention relates to the field of organic synthesis of amino acids, and discloses a method for preparing optically pure N-methyl amino acid ester. Background technique [0002] N-methyl amino acids (NMA) and its derivatives are also important components of many peptide-containing natural products, widely present in peptides, proteins, enzymes and a series of secondary metabolites, such as vancomycin (Vancomycin), Dolastatins (Dolastatins), natural anti-inflammatory cyclic peptide C (CyclomarinC), etc. N-methylamino acid and its peptides can be used as the synthetic unit of many drug research and development due to their physical and chemical stability and low toxicity. The research on the synthesis of NMA has important practical significance and value. Amino acid N-methylation can reduce the number of isomers by limiting the flexibility of the polypeptide molecular skeleton; this structural modification not only affects the interaction between the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/36C07C229/22C07D209/20C07C229/08C07C227/30C07C227/18
Inventor 严间浪谢作王陈振华刘定华宋忆文
Owner 绍兴众昌化工股份有限公司