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Method for preparing Alpha-keto-phenylalanine calcium

A technology of calcium ketophenylalanine and glycine is applied in the field of preparation of calcium α-ketophenylalanine, and can solve the problems of difficult hydrolysis of 5-benzylidene hydantoin, long reaction time, low hydrolysis yield and the like , to achieve the effect of easy reaction control, small equipment investment and high yield

Inactive Publication Date: 2011-05-11
ZHEJIANG NHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic route is relatively simple, and the reaction steps are short, but the hydrolysis of 5-benzylidene hydantoin is difficult, requires a large amount of lye, and the reaction time is long, the conditions are harsh, and the hydrolysis yield is low

Method used

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  • Method for preparing Alpha-keto-phenylalanine calcium
  • Method for preparing Alpha-keto-phenylalanine calcium
  • Method for preparing Alpha-keto-phenylalanine calcium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: Preparation of 4-benzylidene-2-methyldihydrooxazolone

[0045] Put 37.5g (0.5mol) of pharmaceutical grade glycine and 50.5g (0.5mol) of triethylamine into a 500mL three-neck flask equipped with mechanical stirring, thermometer, and reflux condenser, stir evenly, and add dropwise under stirring and cooling control at 50°C 127.5g (1.25mol) of acetic anhydride, after the addition of acetic anhydride is completed, stir and react at 40-50°C for 1 hour, then add 53g (0.5mol) of benzaldehyde dropwise in 15 minutes, and raise the temperature to 100-120°C to continue the reaction 1-2 hours until the benzaldehyde peak disappears, the reaction is complete, the mixture of acetic anhydride, acetic acid, and triethylamine is distilled off under reduced pressure, and can be used in the next batch of reactions after rectification, and the residue is cooled to become a solid 4-methanol. Benzyl-2-methyldihydrooxazolone, weight 88.6g, content 95.5%, yield 90.4%. This conten...

Embodiment 2-6

[0046] Example 2-6: Preparation of 4-benzylidene-2-methyldihydrooxazolone under the same conditions as in Example 1 except that different catalysts were used.

[0047]

Embodiment 7

[0048] Example 7: Preparation of 4-benzylidene-2-methyldihydrooxazolone

[0049] In a 500mL three-neck flask equipped with a mechanical stirrer, a thermometer, and a reflux condenser, put 37.5g (0.5mol) of pharmaceutical grade glycine and 33.3g (0.5mol) of N,N'-dimethylpiperazine, stir evenly, and stir to cool Add 127.5g (1.25mol) of acetic anhydride dropwise under control at 50°C. After the dropwise addition of acetic anhydride is complete, stir and react at 40-50°C for 1 hour, then add 53g (0.5mol) of benzaldehyde dropwise in 15 minutes, and raise the temperature after dropping Continue to react at 100-120°C for 1-2 hours until the peak of benzaldehyde disappears. After the reaction is complete, distill the mixture of acetic anhydride and acetic acid under reduced pressure. Evaporate to dryness under reduced pressure, and cool to obtain a solid of 4-benzylidene-2-methyldihydrooxazolone, with a weight of 88.9 g, a content of 97.5%, and a yield of 92.6%. This content of 4-ben...

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Abstract

The invention discloses a method for preparing a medical material, namely Alpha-keto-phenylalanine calcium. In the conventional methods, some methods are complicate in operation and has low yield, and oxydol is used in the oxidizing process, which is not favorable for safety production; and some methods have long reaction time, harsh conditions and low hydrolysis yield. The preparation method includes the following steps: glycine, benzaldehyde, acetic anhydride and organic base catalyst are taken as raw materials, and 4-benzal-2-methyl dihydride oxazolone is obtained by adopting one-pot method for catalytic cyclization reaction; and 4-benzal-2-methyl dihydride oxazolone and calcium hydroxide conduct ring-opening and hydrolysis reaction in a pressure kettle to obtain Alpha-keto-phenylalanine calcium. The cyclization reaction adopting the one-pot method has low equipment investment and operating cost; organic amine catalyst is easy for reclamation and indiscriminate use; no waste water generates; and the hydrolysis reaction adopting pressurizing reaction has low possibility of side reaction, and the reaction conditions are mild and are easy to control, so that the reaction yield is improved.

Description

technical field [0001] The invention relates to a pharmaceutical raw material, in particular to a preparation method of alpha-ketophenylalanine calcium. Background technique [0002] Calcium α-ketophenylalanine is the main ingredient of compound α-ketoacid tablets. Compound α-ketoacid tablets are used for the treatment of uremia, providing essential amino acids for patients with kidney disease and minimizing the intake of amino nitrogen. Keto or hydroxyamino acids do not contain amino groups themselves, and use the nitrogen of non-essential amino acids to convert them into amino acids, thereby reducing urea synthesis and reducing the accumulation of uremic toxic products. [0003] The structural formula of alpha-ketophenylalanine calcium is as follows: [0004] [0005] At present, there are mainly the following synthetic methods for α-ketophenylalanine calcium: [0006] (1) J.Org.Chem.1963,28 (11): 3088-92 takes ethyl cyanoacetate and benzaldehyde as starting raw mate...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C51/41
CPCY02P20/584
Inventor 钱洪胜鲁国彬董金锋陈洪光冯仪红
Owner ZHEJIANG NHU CO LTD
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