Method for preparing dextrorotary phenylalanine by asymmetric conversion method

A technology of dextro-phenylalanine and phenylalanine is applied in the field of preparation of chiral organic compounds to achieve the effects of improving adaptability, reducing usage, and avoiding entrainment and precipitation

Inactive Publication Date: 2005-11-09
SOUTHEAST UNIV
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, only 50% D-phenylalanine can be obtained theoretically by this method, and the actual total yield is only about 30%

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
  • Method for preparing dextrorotary phenylalanine by asymmetric conversion method

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0014] Example 1 Dissolve the mixture of 6.6g DL-phenylalanine and 6.0g D-tartaric acid in 100.0mL propionic acid, add 1-5% aromatic aldehyde, stir at 70-90°C for 6-8 hours, cool to After cooling at room temperature for 0.5 hours in an ice-water bath, filter and the mother liquor can be recycled. The solid was washed with anhydrous ether and dried to obtain 11.0 g of white crystals of D-tartrate·D-phenylalanine salt, with a yield of 87.7%.

example 2

[0015] Example 2 Dissolve the mixture of 9.9g DL-phenylalanine and 9.0g D-tartaric acid in 120.0mL propionic acid, and others are the same as example 1 to obtain 15.60g of white crystals of D-tartaric acid D-phenylalanine salt, Yield 82.5%. Then D-phenylalanine can be prepared from D-tartaric acid·D-phenylalanine salt.

[0016] Example 3 Dissolve the D-tartrate·D-phenylalanine salt obtained in Example 1 in 9.86ml of triethylamine and 67ml of absolute ethanol, stir at room temperature for 1 hour, then cool to 5-10°C, filter and wash the solid with an appropriate amount of ethanol 1 to 3 times to obtain 4.66 g of D-phenylalanine as a white solid with a yield of 80.5%. [α] D 20 =+33.7°.

example 4

[0017] Example 4. Dissolve 11.05 g of D-tartaric acid D-phenylalanine salt in 9.86 ml of triethylamine and 67 ml of methanol, stir at room temperature for 1 hour, then cool to 5-10°C, filter and wash the solid with an appropriate amount of methanol for 1- Three times, 4.24 g of white solid D-phenylalanine was obtained, and the yield was 73.2%.

[0018] Example 5 Dissolve 11.05 g of D-tartrate·D-phenylalanine salt in 5 times the amount of water, add 2 times the amount of concentrated ammonia water, stir at room temperature for 1 hour, cool to 5-10°C, filter and wash with appropriate amount of cold water Solid 1 to 3 times. The solid obtained after concentrating the mother liquor was combined with the aforementioned solid to obtain 4.14 g of D-phenylalanine crystals, with a yield of 71.5%.

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 method for preparing D-phenylalanine by using DL-phenylalanine includes the following steps: firstly, mixing DL-phenylalanine and D-tartaric acid according to the mole ratio of 1:1.5-1.5:1 and dissolving them in organic solvent, adding 1.0-5.0% of aromatic alolehyde catalyst and making reaction for 6-8 hr. at 70-90 deg.C, cooling by using ice water bath, filtering, using anhydrous ethyl ether to wash and drying to obtain D-tartaric acid: D-phenylalanine salt, then dissolving the above-mentioned product in solvent, adding ammonization agent to make ammonization while stirring, after 1 hr. cooling to 5 deg.C-10 deg.C, filtering and washing with solvent so as to obtain the invented D-phenylalanine.

Description

technical field [0001] The invention is a preparation method of a chiral organic compound, in particular a method for preparing D-phenylalanine (D-phenylalanine) from DL-phenylalanine. Background technique [0002] D-Phenylalanine is an important chiral amino acid with many uses. For example, it is used to produce heterocyclic dipeptide derivatives that promote hormone release, thrombin inhibitors, endopeptidase inhibitors, HIV inhibitors and other pharmaceutical intermediates. In addition, D-phenylalanine itself can also be used as an anti-inflammatory analgesic, HIV inhibitor, anti-stress agent and diabetes control agent, and can also be used as a chiral reagent or chiral intermediate. At present, most of the production of D-phenylalanine is to prepare DL-phenylalanine by synthetic method, and then obtain it by resolution. Therefore, the resolution of DL-phenylalanine is an important step in the production process of D-phenylalanine. [0003] At present, the most common...

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 Patents(China)
IPC IPC(8): C07C227/30C07C229/36
Inventor 蒋立建未本美郑颖平徐海青邹建忠张征林
Owner SOUTHEAST UNIV
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
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap