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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, and achieves the effects of simplifying post-processing procedures, avoiding entrainment and precipitation, and reducing production costs

Inactive Publication Date: 2003-05-21
SOUTHEAST UNIV
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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

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0011] 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

[0012] Example 2 The mixture of 9.9g DL-phenylalanine and 9.0g D-tartaric acid was dissolved in 120.0mL propionic acid, and the others were the same as in Example 1 to obtain 15.60g of white crystals of D-tartaric acid D-phenylalanine salt. Yield 82.5%.

[0013] Then D-phenylalanine can be prepared from D-tartaric acid·D-phenylalanine salt.

example 3

[0014] 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°.

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PUM

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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 etherto 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

1. 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. 2. Background technology [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...

Claims

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Application Information

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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
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