Synthesis method of alkylglycine

Abstract

The invention discloses a synthesis method of alkylglycine. According to the method, N-(diphenylmethylene)aminoacetonitrile is used as a raw material to take a substitution reaction with 2-alkyl halide under the effect of a catalyst of lithium diisopropylamide so as to synthesize a fire-new intermediate compound of (3S)-2-((diphenylmethylene)amino)-3-methylalkyl nitrile. The method can be appliedto the synthesis of alkylglycine such as isoamylglycine, isohexyl glycine and isoheptyl glycine; products can be used as necessary intermediates for pesticides and medicine. By using the synthesis method provided by the invention, the raw material price is low; the production cost is low; the product purity is high; the reaction steps are simple; the reaction speed is high; the conditions are mild; the reaction treatment is simple and convenient; the method is more suitable for mass production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of alkyl glycine. Background technique [0002] Alkylglycine such as isopentylglycine is a series of unnatural amino acids. Isopentylglycine can also be named 2-amino-3-methylhexanoic acid or 3-methylnorleucine. Its structural formula is as follows: [0003] [0004] Regarding the synthetic method of isopentylglycine, there are related reports in domestic and foreign literatures, but the synthetic routes of these reports all use enzyme-catalyzed synthesis, for example: (2RS, 3RS)- 2-Amino-3-methylhexanoic acid in Trichomonas D-amino acid oxidase and NaBH 4 or NaCNBH 3 (2S, 3S)-2-amino-3-methylhexanoic acid and (2S, 3R)-2-amino-3-methylhexanoic acid were obtained under the action of a reducing agent. And also studied the effect of L-isoleucine on amino acid oxidase and NH 3 :BH 3 or Pd / C–HCO 2 NH 4 Under the action, it is converted into (...

AI Technical Summary

Problems solved by technology

Use catalyst N,N-dimethylformamide to control relatively strict synthetic conditions in the synthesis of 2-(diphenylmethylene)amino-2-methylpropionitrile, and the test treatment is more complicated. The by-product synthesized by this method There are many types, the separation of products is complicated, and the purity is not high

People such as Alexis Enright of the University of Edinburgh in the United Kingdom used n-butyllithium as a catalyst to catalyze the alkylation reaction of N-(dibenzylidene) aminoacetonitrile and bromobutane, but n-butyllithium was not only difficult to operate as a catalyst, but the reaction solution treatment More troublesome, product separation is difficult, not suitable for the synthesis of (3S)-2-((dibenzylidene)amino)-3-methylcapronitrile

In addition, many similar reactions use enzymes as catalysts, and the cost of this method is relatively high due to the high price of enzymes

Although similar compounds have been synthesized before, the synthesis method is not suitable for 2-haloalkanes, not only the reaction time is longer, the reaction by-products are more, the reaction treatment is more troublesome, and some reactions even have higher costs

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