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A kind of preparation method and application of (3r,4s)-4-ethylpyrrolidine-3-carboxylic acid compound

An ethylpyrrolidine and compound technology, applied in the field of pharmaceutical synthesis, can solve problems such as low yield and high cost, and achieve the effects of simple synthesis route, low synthesis cost, and simple and easy-to-obtain raw materials

Active Publication Date: 2021-06-04
北京海美桐医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] To this end, the embodiment of the present invention provides a preparation method and application of (3R,4S)-4-ethylpyrrolidine-3-carboxylic acid compounds, so as to solve the existing synthetic methods that require the use of highly toxic or strong corrosive reagents, lower yields due to chiral resolution, and high cost

Method used

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  • A kind of preparation method and application of (3r,4s)-4-ethylpyrrolidine-3-carboxylic acid compound
  • A kind of preparation method and application of (3r,4s)-4-ethylpyrrolidine-3-carboxylic acid compound
  • A kind of preparation method and application of (3r,4s)-4-ethylpyrrolidine-3-carboxylic acid compound

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Embodiment

[0046] (3R, 4S) -4- ethyl-pyrrolidine-3-carboxylic acid compounds, comprising the steps of:

[0047] (1) Synthesis of Compound 1

[0048] Its reaction equation is as follows:

[0049]

[0050]73.8 g of glycine ethyl ester was dissolved in 500 ml of dichloromethane in 1000 ml of reaction flask, and 144.8 g of triethylamine was added dropwise thereto at 0 ° C, and the dropwise addition was added, and 74.52 g of methyl chloroformate was added dropwise. After the reaction was allowed to at room temperature, after 3 h, 100 ml of aqueous hydrochloric acid solution (1 m), a liquid, and the organic phase was sequentially washed with saturated brine and water, dried over anhydrous sodium sulfate, filtered, evaporated. The compound 1 was obtained directly for the next reaction.

[0051] (2) Synthetic Compound 2

[0052] Its reaction equation is as follows:

[0053]

[0054] The compound 1 obtained by step (1) is dissolved in 400 ml of tetrahydrofuran, then 72 g of ethyl acrylate, drown ...

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Abstract

The embodiment of the invention discloses a preparation method and application of a (3R,4S)-4-ethylpyrrolidine-3-carboxylic acid compound, which relates to the technical field of drug synthesis. In the present invention, ethyl glycine is used as a raw material, and (3R,4S)-4-ethylpyrrolidine-3-carboxylate is synthesized sequentially through amino group protection, ring closure, substitution, coupling, catalytic hydrogenation, hydrolysis and deprotection acid. The target product synthesized by this reaction has high yield and chiral purity, and also has the advantages of simple and easy-to-obtain raw materials, simple synthesis route, mild reaction conditions, simple separation and purification operation, and low synthesis cost.

Description

Technical field [0001] Embodiments of the present invention relate to the art of drug synthesis, and therefore, in particular, a method of preparation of (3R, 4S) -4-ethylpyrrolidine-3-carboxylic acid compounds and its application thereof. Background technique [0002] UpadacitiniB is an Oral-Oral Jak1 selective inhibitor developed by Albevi, which was approved by FDA in August 2019 for treatment of rheumatoid arthritis. JANUS Kinase is a cellular non-acceptable tyrosine kinase family that mediates signals produced by cytokines, and passes through Jak-STAT signaling pathways, including JAK1, JAK2, JAK3, TYK2 four members, Plays an important role in the signal transduction of the cytokine receptor superfamily members. JAK play an important role in immune-mediated disease pathology, which can be used to treat some autoimmune diseases such as the treatment of specialty dermatitis, rheumatoid arthritis, psoriasis, ulcerative colitis, and the like. [0003] Among them (3R, 4S) -4-ethy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/16
CPCC07D207/16Y02P20/55
Inventor 张同波刘艳玲张旭
Owner 北京海美桐医药科技有限公司
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