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Chemical synthesis method of chiral D-phenylalanine

A technology for chemical synthesis of phenylalanine, applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of complex process, low optical purity of products, high cost, etc., and achieve simple production process operation and high product quality The effect of high optical purity and wide application range

Inactive Publication Date: 2011-11-09
北京金源化学集团有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Due to the complex process and high cost of producing D-phenylalanine at present, it is not suitable for industrialized production, and the optical purity (ee%) of the product is low, which cannot meet the needs of drug synthesis

Method used

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  • Chemical synthesis method of chiral D-phenylalanine
  • Chemical synthesis method of chiral D-phenylalanine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] a): Add 8.2 g of acetamidocinnamic acid ((Z)-2-acetamido-3-phenyl-acrylic acid) and 200 ml of methanol into the autoclave. The reactor was installed and filled with nitrogen. The nitrogen pressure was maintained at 0.7Mpa, and the reactor was stirred for 30 minutes to completely degas the solvent. Then deflate. Add the chiral catalyst ([Rh(1,5-cyclooctadiene)((1R,2R)-bis[(2-methoxyphenyl)phenylphosphine]ethane)]BF4) and a small amount of methanol solution . The reactor was filled with hydrogen, replaced 3 times, and then filled with hydrogen, the pressure was maintained at 1MPa, the internal temperature of the reactor was 30°C, and the reaction was carried out for 8 hours. During the reaction, when the hydrogen pressure was lower than 1MPa, continue to add hydrogen. Then deflate, refill with nitrogen, stir for 30 minutes, release nitrogen, pour out the reaction solution, filter, and evaporate the solvent to dryness to obtain acetamido-D-phenylalanine (II) with a yiel...

Embodiment 2

[0021] a): Add 8.2 g of acetamidocinnamic acid ((Z)-2-acetamido-3-phenyl-acrylic acid) and 200 ml of methanol into the autoclave. The reactor was installed and filled with nitrogen. The nitrogen pressure was maintained at 0.7Mpa, and the reactor was stirred for 30 minutes to completely degas the solvent. Then deflate. The chiral catalyst ([Rh(1,5-cyclooctadiene)((1R,2R)-bis[(2-methoxyphenyl)phenylphosphine]ethane)]BF 4 ) and a small amount of methanol solution were added. The reactor was filled with hydrogen, replaced 3 times, then filled with hydrogen, the pressure was maintained at 3MPa, the internal temperature of the reactor was 30°C, and the reaction was carried out for 5 hours. During the reaction, when the hydrogen pressure was lower than 3MPa, continue to add hydrogen. Then deflate, refill with nitrogen, stir for 30 minutes, release nitrogen, pour out the reaction solution, filter, and evaporate the solvent to dryness to obtain acetamido-D-phenylalanine (II) with a ...

Embodiment 3

[0026] In the same manner as in Example 1, 4-chloro-D-phenylalanine was prepared using (Z)-2-acetylamino-3-(4-chlorophenyl)-acrylic acid raw material. 1 H-NMR (D 2 O), δ2.86-2.97ppm (2H, CH 2 ), 3.91ppm (1H, CH), 7.17ppm (2H, C 6 h 5 ), 7.20ppm (2H, C 6 h 5 ). Yield 81%.

[0027] Product 4-chloro-D-phenylalanine Chemical purity: (HPLC): ≥98.95%

[0028] Optical purity: (HPLC, e.e%): ≥99%

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Abstract

The invention relates to a chemical synthesis method for preparing chiral D-phenylalanine. The chemical synthesis method comprises the following reaction steps: (a) carrying out hydrogenation reduction on acetamidocinnamic acid and derivatives thereof (I) in the presence of a chiral catalyst to obtain acetamido-D-phenylalanine (II), and (b) carrying out hydrolysis reaction on the acetamido-D-phenylalanine to remove acetyl, thus obtaining D-phenylalanine (III).

Description

technical field [0001] The invention relates to a chemical synthesis method of unnatural chiral D-phenylalanine. Background technique [0002] As an important chiral compound, D-phenylalanine is an important raw material for the synthesis of gramicidin S and other polypeptide antibiotics. It can be used as an intermediate of various drugs such as heterocyclic polypeptide drugs, analgesics, sedatives, antineoplastic drugs, anti-AIDS drugs, hypoglycemic and cardiovascular drugs, weight loss drugs, and nutritional health products. [0003] As an important pharmaceutical and pesticide intermediate, D-phenylalanine is widely used in the fields of medicine, pesticide, food, feed, etc., and its market demand continues to increase. Therefore, it is necessary to look for D-phenylalanine with simple process and low cost. The preparation method of amino acid is very necessary. At present, the methods for preparing D-phenylalanine mainly include enantiomer resolution, asymmetric chemi...

Claims

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Application Information

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IPC IPC(8): C07C229/36C07C227/32C07C227/20B01J31/24
Inventor 张和平李海滨邱明建陈朝晖李丽霞赵磊张雅丽于淑利
Owner 北京金源化学集团有限公司
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