Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of N, N-bis (2-chloroethyl)-4-nitrophenyl alanine methyl ester

A technology of nitrophenylalanine methyl ester and chloroethyl, which is applied in the field of preparation of N,N-di-4-nitrophenylalanine methyl ester, can solve problems such as no preparation method, and achieves The effect of the simple operation of the reaction

Pending Publication Date: 2022-05-31
CHEMSHUTTLE
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, N,N-di(2-chloroethyl)-4-nitrophenylalanine methyl ester has the report of this compound, but there is no synthetic preparation method

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 N, N-bis (2-chloroethyl)-4-nitrophenyl alanine methyl ester
  • Preparation method of N, N-bis (2-chloroethyl)-4-nitrophenyl alanine methyl ester
  • Preparation method of N, N-bis (2-chloroethyl)-4-nitrophenyl alanine methyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A preparation method of N,N-bis(2-chloroethyl)-4-nitrophenylalanine methyl ester, the preparation method comprising the steps of:

[0025] Compound 1 (N,N-bis(2-hydroxyethyl)-4-nitrophenylalanine) (6.0g, 0.02mol) was added to 200mL of methanol, and slowly added 0.5 mL of 18mol / L concentrated sulfuric acid, then warmed up to 60°C and stirred for 24 hours. After the reaction was detected by TLC, it was concentrated to dryness by distillation under reduced pressure, and purified by column (200-300 mesh silica gel), using dichloromethane: Methanol = 40:1 solvent for isocratic elution, the product part was collected, concentrated to dryness under reduced pressure to obtain a yellow solid, that is, the compound 2(N,N-bis(2-hydroxyethyl)-4-nitro Phenylalanine methyl ester) crude product 5.6g, directly used in the next step of chlorination without further purification.

[0026] The LCMS spectrum of compound 2 is as follows figure 1 Shown, in the figure A: ion flow chart; B: t...

Embodiment 2

[0030] A preparation method of N,N-bis(2-chloroethyl)-4-nitrophenylalanine methyl ester, the preparation method comprising the steps of:

[0031] Compound 1 (N,N-bis(2-hydroxyethyl)-4-nitrophenylalanine) (6.0g, 0.02mol) was added to 10mL of methanol, and 5.5 mL of 18mol / L concentrated sulfuric acid, then heated up to 80°C and stirred for 4 hours. After the reaction was detected by TLC, it was concentrated to dryness by distillation under reduced pressure, and then purified by column (200-300 mesh silica gel), using dichloromethane: Methanol = 40:1 solvent for isocratic elution, the product part was collected, concentrated to dryness under reduced pressure to obtain a yellow solid, that is, the compound 2(N,N-bis(2-hydroxyethyl)-4-nitro Phenylalanine methyl ester) crude product 5.2g, directly used in the next step of chlorination without further purification.

[0032] Compound 2 (N,N-bis(2-hydroxyethyl)-4-nitrophenylalanine methyl ester) (5.2g, 0.017mol) was slowly added in ba...

Embodiment 3

[0034] Compound 1 (N,N-bis(2-hydroxyethyl)-4-nitrophenylalanine) (6.0g, 0.02mol) was added to 100mL of methanol, and 2.5 mL of 18mol / L concentrated sulfuric acid, then heated up to 80°C and stirred for 4 hours. After the reaction was detected by TLC, it was concentrated to dryness by distillation under reduced pressure, and then purified by column (200-300 mesh silica gel), using dichloromethane: Methanol = 40:1 solvent for isocratic elution, the product part was collected, concentrated to dryness under reduced pressure to obtain a yellow solid, that is, the compound 2(N,N-bis(2-hydroxyethyl)-4-nitro Phenylalanine methyl ester) crude product 5.5g, directly used in the next step of chlorination without further purification.

[0035] Compound 2 (N,N-bis(2-hydroxyethyl)-4-nitrophenylalanine methyl ester) (5.5g, 0.018mol) was slowly added in batches to phosphorus oxychloride (85mL, 0.87mol ), then heated up to 95°C and stirred for 12 hours. After the reaction was detected by TLC,...

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 N, N-bis (2-chloroethyl)-4-nitrophenyl alanine methyl ester, and belongs to the technical field of synthesis of medical intermediates. The preparation method comprises the following steps: (1) dissolving a compound 1 in methanol, adding concentrated sulfuric acid, and heating for esterification reaction to prepare a compound 2; and (2) dissolving the compound 2 in phosphorus oxychloride, and heating to carry out chlorination reaction to prepare a target product, namely the N, N-bis (2-chloroethyl)-4-nitrophenyl alanine methyl ester. The method is simple to operate and relatively high in yield, and a target product with very high purity is obtained.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of N,N-bis(2-chloroethyl)-4-nitrophenylalanine methyl ester. Background technique [0002] Drug molecular building blocks are important fragments that make up drug molecules, just like Lego building blocks, and are the raw materials for the synthesis of drug molecules. The N,N-bis(2-chloroethyl)-4-nitrophenylalanine methyl ester synthesized by this method, because phenylalanine compounds are extremely important chemical fragments in medicinal chemistry, thus in organic It has very important application prospects in the fields of chemistry, biomedicine, medicine and pesticide intermediates. Phenylalanine esters contained in such compounds are extremely valuable synthetic building blocks in synthesis. [0003] Phenylalanine compounds have therapeutic and preventive activities for metabolic diseases, and can be used to treat d...

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
IPC IPC(8): C07C227/16C07C227/18C07C229/36
CPCC07C227/16C07C227/18C07B2200/07C07C229/36
Inventor 李欢
Owner CHEMSHUTTLE
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap 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