Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Preparation method of tryptophan derivative medical intermediate

A technology of derivatives and tryptophan, applied in the field of preparation of tryptophan derivative pharmaceutical intermediates, can solve problems such as unreported preparation methods, achieve easy industrial production, high product yield and purity, and simple preparation process Effect

Pending Publication Date: 2021-09-17
ZHEJIANG UNIV OF TECH
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, there is no report on the preparation method of N-alpha-fluorenylmethoxycarbonyl-N-in-tert-butoxycarbonyl-L-tryptophan derivatives

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of tryptophan derivative medical intermediate
  • Preparation method of tryptophan derivative medical intermediate
  • Preparation method of tryptophan derivative medical intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] The synthetic scheme one of preparing tryptophan derivative pharmaceutical intermediate (I) among the present invention is as follows:

[0045]

[0046] (1) Preparation of L-tryptophan methyl ester (Ⅲ-a)

[0047] Add L-tryptophan (4.085g, 20mmol) and 40mL of methanol into a 100mL three-neck flask equipped with magnetic stirring and a thermometer, and slowly add thionyl chloride (4.758g, 40mmol) dropwise under an ice bath at -10°C. Ensure that the temperature of the reaction solution is below room temperature, and after the dropwise addition is completed, the temperature is raised to reflux for esterification reaction, and TLC monitors the end of the reaction. Cool, concentrate to remove methanol, add saturated sodium bicarbonate solution to alkalinize to pH 8-9, add dichloromethane for extraction (3×20ml), take the organic layer and wash with water (2×15ml), dry over anhydrous sodium sulfate, and concentrate Finally, 4.348 g of yellow oily substance L-tryptophan met...

Embodiment 2

[0087] The synthetic scheme two of preparing tryptophan derivative pharmaceutical intermediate (I) among the present invention is as follows:

[0088]

[0089] (1) Preparation of L-tryptophan methyl ester (Ⅲ-a)

[0090] The preparation process of L-tryptophan methyl ester (III-a) in Example 2 was repeated in Example 1.

[0091] (2) Preparation of N-alpha-benzyloxycarbonyl-L-tryptophan methyl ester (VII-a)

[0092] Add L-tryptophan methyl ester (2.183g, 10mmol) and 20mL of tetrahydrofuran into a 100mL two-necked flask with magnetic stirring and a thermometer, and then dissolve sodium carbonate (1.272g, 12mmol) in water (20ml) to prepare Concentration is about 6% sodium carbonate aqueous solution, then sodium carbonate aqueous solution is added to the reaction solution, after mixing, N-benzylsuccinimide carbonate (2.492g, 10mmol) is added, and the reaction is carried out at room temperature, and TLC monitors the end of the reaction . Separate the layers, wash the organic p...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of a tryptophan derivative medical intermediate. comp The method comprises the following steps: by taking an L-tryptophan derivative as an initial raw material, sequentially carrying out esterification, amidation, Boc protection, hydrolysis and amidation or sequentially carrying out esterification, amidation, Boc protection, hydrogenation, hydrolysis and amidation to prepare a target product, namely, the tryptophan derivative medical intermediate. The preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, environmental friendliness, less three wastes in the process, mild reaction conditions, simple process, simplicity and convenience in operation, high yield and purity and easiness in large-scale production, and conforms to the concept of green pharmacy.

Description

technical field [0001] The invention belongs to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of tryptophan derivative pharmaceutical intermediates. Background technique [0002] Amino acid is the most basic substance that constitutes the protein needed for the nutrition of organisms. It has remarkable physiological characteristics in the body and is one of the indispensable nutrients for organisms. Amino acids are widely used, such as food, medicine, feed, etc. [0003] Polypeptide drugs have the advantages of high activity, stable curative effect, less toxic and side effects, less dosage, and specific action targets. ,with broadly application foreground. However, natural peptide drugs have been unable to meet the needs of clinical applications due to limitations such as low content and low purity. At present, the introduction of unnatural amino acid structural units is a very effective method to overcome the inher...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/26
CPCC07D209/26
Inventor 李坚军胡思雅贺志良张其伟刘菲菲
Owner ZHEJIANG UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com