Process of one-step hydrogenation synthesis of alpha-substd. beta-amino acid

Abstract

A one-step hydrogenating process for synthesizing beta-amino acid with substituent at its alpha position includes proportionally feeding aldehyde and ethyl cyanoacetate into flask, adding absolute alcohol, stirring while adding dropwise diethylamine, standing for 3-24 hr, adding water, stirring, filtering, drying, adding Raney Ni, acetic anhydride and sodium acetate, hydrogenating at 50-80 deg.C and 5-8 MPa for 16-24 hr, filtering to remove Raney Ni, evaporating out solvent, adding concentrated sulfuric acid, reflux for 0-16 hr, neutralizing with solution of sodium hydroxide, washing and drying.

Description

technical field [0001] The invention belongs to the technical field of synthesizing unnatural amino acids, in particular to a general synthesis method of β-amino acid series with substituents at the β position. Background technique [0002] The natural amino acids that make up proteins in nature are all α-amino acids. Their parent structural formula is H 2 N-CH 2 -COOH. In contrast, the parent structure of β-amino acids is NH 2 -CH 2 -CH 2 -COOH. Compared with α-amino acid, there is one more methylene group between amino group and carboxyl group in β-amino acid molecule. The hydrogens on the amino acid methylene can be replaced by various side chain substituents, which makes β-amino acids have more structural diversity than α-amino acids. Although beta-amino acids are not involved in the construction of natural substances such as proteins, this does not mean that they are completely absent in nature. For example, Wasvisz et al. reported that some macrocyclic polypep...

AI Technical Summary

Problems solved by technology

[0016] The synthesis methods of β-amino acids mentioned above all have problems such as many synthesis steps, difficult separation and purification, expensive reagents, and limited scale-up synthesis.