Process for synthesizing L-2,4-dinitrophenyl alanine

A technology of dinitrophenylalanine and nitrophenylalanine, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve difficulties in unsuitable for large-scale production, side reactions, and separation of mixtures etc. to achieve the effects of low production cost, mild reaction conditions, and easy availability of raw materials

Inactive Publication Date: 2012-06-06
ZHEJIANG UNIV
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Problems solved by technology

[0005] Its document synthesis method is as follows: document Analytica Chimica Acta, 19 (1): 90-100, (1958) is to analyze phenylalanine, with K 2 NO 3 / H 2 SO 4 As a nitrating reagent, it was reacted at 100°C for 1 h, and the resulting reaction mixture was treated with SnCl 2 After reduction analysis, it is considered that 2,4-dinitrophenylalanine has been obtained, but this method is only used to analyze phenylalanine, and the reaction only uses 33 mg and is not suitable for the preparation of 2,4-dinitrophenylalanine. phenylalanine, because this method is only used for analysis, and the content of 2,4-dinitrophenylalanine in the mixture is only 60%, and there are serious side reactions, and the oxidation product 2 , 4-dinitrobenzoic acid and 3,5-dinitrobenzoic acid are difficult to remove in this system, and the separation of the mixture obtained by the reaction is very difficult. It needs to be separated by column chromatography and other methods, which is not suitable for large-scale production

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  • Process for synthesizing L-2,4-dinitrophenyl alanine
  • Process for synthesizing L-2,4-dinitrophenyl alanine

Examples

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Embodiment 1

[0017] Embodiment 1, a kind of synthetic method of L-2,4-dinitrophenylalanine, carries out following steps successively:

[0018] 1) Add 60g (1.0mol) of urea to 100mL of 63% concentrated nitric acid (1.0mol) at room temperature (25°C). After complete addition, react for 1h and cool in an ice-water bath (0°C) to obtain 121.0g of urea nitrate , yield 98%.

[0019] 2), at 10°C, dissolve 21.0 g of L-4-nitrophenylalanine (0.10 mol) in 50 mL of concentrated sulfuric acid (98% w), then add 14.7 g of urea nitrate prepared in step 1) ( 0.12mol), the reaction was continued for 20h at this temperature. After adjusting the pH of the obtained reaction solution to 7.0 with ammonia water, the obtained solution was dehydrated, and then the obtained solid was recrystallized with 500 mL of methanol, and the yellow solid precipitated from the mother liquor was L-2,4-dinitrobenzene Alanine, a total of 19.7g (yield 77.3%).

[0020] The reaction conditions in Example 1 were changed to obtain Exa...

Embodiment 5

[0023] Embodiment 5, a kind of synthetic method of L-2,4-dinitrophenylalanine, carries out following steps successively:

[0024] 1), at room temperature, 123g (1.0mol) of urea nitrate was added to 200mL of concentrated sulfuric acid (98%w). After the urea nitrate was completely dissolved, the reaction was continued for 1h, and the resulting reaction solution was poured into 500g of ice water to precipitate White solid nitrourea 100g, yield 95.2%.

[0025] 2), at 10°C, dissolve 21.0 g of L-4-nitrophenylalanine (0.10 mol) in 50 mL of concentrated sulfuric acid (98% w), and then add 12.6 g of nitrourea prepared in step 1) (0.12mol), the temperature continued to react for 20h. After the obtained reaction solution was adjusted to pH 7.0 with sodium hydroxide, the obtained solution was dehydrated, and then the obtained solid was recrystallized with 500 mL ethanol to obtain L-2, 23.5 g of 4-dinitrophenylalanine ( Yield 92.2%).

[0026] The reaction conditions in Example 5 were ch...

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Abstract

The invention discloses a method for synthesizing L-2, 4-dinitrobenzene lactamine. L-4-nitrobenzene lactamine is dissolved in concentrated sulfuric acid, and urea nitrate or nitrourea is added to react for 1-20 hours at the temperature of 0-100 DEG C. The mol ratio of the urea nitrate or nitrourea and the L-4-nitrobenzene lactamine is 1.2-3.0:1. An obtained reaction product is put into ice water;then pH is adjusted to neutral by alkaline substance; solvent is removed; residual solid is recrystallized by saturated fatty alcohol; and separated yellow solid is the L-2, 4-dinitrobenzene lactamine. The method for producing the L-2, 4-dinitrobenzene lactamine is characterized by good safety, convenient operation and high yield.

Description

technical field [0001] The invention relates to a synthesis method of an organic compound, in particular to a synthesis method of L-2,4-dinitrophenylalanine, an organic chemical intermediate. Background technique [0002] L-2,4-dinitrophenylalanine is an important organic chemical intermediate, which plays a very important role in the synthesis of some optically active chiral drugs. The structural formula is shown in formula 1: [0003] [0004] Formula 1 [0005] Its document synthesis method is as follows: document Analytica Chimica Acta, 19 (1): 90-100, (1958) is to analyze phenylalanine, with K 2 NO 3 / H 2 SO 4 As a nitrating reagent, it was reacted at 100°C for 1 h, and the resulting reaction mixture was treated with SnCl 2 After reduction analysis, it is considered that 2,4-dinitrophenylalanine has been obtained, but this method is only used to analyze phenylalanine, and the reaction only uses 33 mg and is not suitable for the preparation of 2,4-dinitrophenylal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/36C07C227/16
Inventor 陈新志刘金强钱超
Owner ZHEJIANG UNIV
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