A kind of preparation method of 2,3-diaminopropionic acid methyl ester

Abstract

The invention provides a method for preparing methyl 2,3-diaminopropionate, which uses serine as a raw material, uses thionyl chloride as a catalyst in methanol to prepare methyl serine, and then reacts with triphenylchloromethane to form Intermediate product 1, introduces Trt group, intermediate product 1 uses anhydrous tetrahydrofuran as solvent, under the catalysis of triphenylphosphine and DIAD, reacts with phthalimide to generate intermediate product 2, introduces Pht group, intermediate The Pht group of the product 2 was removed under the action of hydrazine hydrate to generate the intermediate product 3, and the Trt group of the final intermediate product 3 was removed in hydrochloric acid ethanol to obtain the final product 4.

Description

technical field [0001] The invention belongs to the field of compound preparation, and in particular relates to a preparation method of methyl 2,3-diaminopropionate. Background technique [0002] During the research and development of peptide inhibitors of cysteine ​​proteases, Pfizer synthesized a series of classic peptidomimetic inhibitors (the structure of which is shown in the structural formula), which are mainly used to inhibit the common cold and respiratory and intestinal diseases. Single-positive-sense RNA viruses that replicate for human diseases, such as human rhinovirus (HRV) in the picornavirus family and norwalk virus (NV) in the family Caliciviridae. Since the binding sites of human rhinovirus 3C protease (HRV 3CP) and Norwalk virus protease (NVPro) in these two viruses have a similar and highly conserved His-Cys-Glu catalytic triad for specific catalytic cleavage The Gln-Gly peptide bond is therefore considered a potential target protein. Most of the P1 seg...

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Problems solved by technology

But these methods more or less have some deficiencies, such as the reaction conditions are not mild, the starting materials are difficult to obtain and the synthetic route is loaded down with trivial details etc.

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