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Preparation method of 2,3-diamido methyl propionate

A technology of methyl diaminopropionate and methyl serine, which is applied in the field of compound preparation, can solve problems such as mild reaction conditions, cumbersome synthetic routes, and difficulty in obtaining starting materials, and achieve the effect of mild reaction conditions and high yield

Active Publication Date: 2019-01-22
NINGXIA MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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.

Method used

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  • Preparation method of 2,3-diamido methyl propionate
  • Preparation method of 2,3-diamido methyl propionate
  • Preparation method of 2,3-diamido methyl propionate

Examples

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Embodiment 1

[0037] In this example, serine is used as a raw material, and the active ester generated by thionyl chloride and methanol is used in methanol to prepare serine methyl ester, which is then reacted with triphenylchloromethane to generate intermediate product 1, and the Trt group is introduced. Intermediate product 1 is Anhydrous tetrahydrofuran as a solvent, under the catalysis of triphenylphosphine and diisopropyl azodicarboxylate DIAD (molecular formula: (CH3)2CHOOCN=NCOOCH(CH3)2), reacts with phthalimide to form The Pht group was introduced into the intermediate product 2, the Pht group was removed from the intermediate product 2 under the action of hydrazine hydrate to generate the intermediate product 3, and the Trt group was finally removed from the intermediate product 3 in hydrochloric acid ethanol to obtain the final product 4.

[0038] The specific process is as follows:

[0039] (1) Synthesis of serine methyl ester:

[0040] Add 30ml of methanol to a 100ml flask, sti...

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Abstract

The invention provides a preparation method of 2,3-diamido methyl propionate. According to the method, serine is used as a raw material, in methyl alcohol, thionyl chloride is used as a catalyst for preparing serine methylester, then the serine methylester is reacted with triphenyl chloromethane to generate an intermittent product 1, a Trt group is introduced, anhydrous tetrahydrofuran is used asa solvent of the intermittent product 1, under catalysis of triphenylphosphine and DIAD, the intermittent product 1 is reacted with phthalimide to generate an intermittent product 2, a Pht group is introduced, under hydrazine hydrate action, the Pht group is removed from the intermittent product 2 to generate an intermittent product 3, and finally, in hydrochloric acid alcohol, the Trt group is removed from the intermittent product 3 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 is shown in the figure below), which are mainly used to inhibit the Disease replication by single positive-sense RNA viruses such as human rhinovirus (HRV) in the family of picornaviruses 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 P 1 segment of such peptidomimetic inhibitors have (S)-2-amino-3-acetylaminopropi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C229/26
CPCC07C227/16C07C227/18C07D209/48C07C229/26C07C229/22
Inventor 黄宇王英樊艳茹
Owner NINGXIA MEDICAL UNIV
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