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Synthetic method of unnatural tryptophan derivative

A synthesis method and technology for derivatives, which are applied in the field of synthesis and preparation of non-natural tryptophan derivatives, can solve the problems of high raw material prices, harsh reaction conditions, and many steps in the synthesis of non-natural tryptophan derivatives, and achieve raw material costs low effect

Active Publication Date: 2019-05-07
上海毕得医药科技股份有限公司
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The technical problem solved by the present invention is that in the prior art, there are many synthetic steps of unnatural tryptophan derivatives, the price of raw materials is high, and the reaction conditions are harsh

Method used

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  • Synthetic method of unnatural tryptophan derivative
  • Synthetic method of unnatural tryptophan derivative
  • Synthetic method of unnatural tryptophan derivative

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Effect test

Embodiment 1

[0027] The reaction synthesis route of 5-bromo-DL-tryptophan is as follows:

[0028]

[0029] (1) Preparation of Compound 2

[0030]

[0031] Dissolve 5-bromo-indole compound 1 (200g, 1.02mol), ethyl 2-azidoacrylate (151.01g, 1.07mol), bismuth trifluoromethanesulfonate (33.5g, 0.05mol) in 1200ml In acetonitrile, react at room temperature for 3 hours. After TCL detects that the reaction is complete, quench the reaction with water, extract the reaction solution twice with ethyl acetate 600ml*2, combine the organic phases, wash with saturated brine, and then add anhydrous sodium sulfate to dry. The organic phase was concentrated to obtain the crude product compound 2 (292.3 g), with a yield of about 85%.

[0032] (2) Preparation of compound 3

[0033]

[0034] The compound 3 (250g, about 0.74mol) obtained in the previous step was dissolved in 1500ml of methanol, and then an aqueous solution (1mol / L) of KOH (124.56, 2.22mol) was added dropwise. After the dropwise additi...

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Abstract

The invention relates to the field of organic synthesis, and discloses a non-natural tryptophan derivative synthesis method. Indole derivatives serve as raw materials. The synthesis method includes the steps: (1) dissolving the indole derivatives, 2-nitrine ethyl acrylate and bismuth trifluoromethanesulfonate in organic solvents, performing reaction for 2-6 hours, performing quenching reaction after complete reaction, extracting reaction liquid, and washing and drying an organic phase to obtain a compound 2; (2) dissolving the compound 2 in alcohol, dripping alkali solution, continuing reaction for 1.5-5 hours, performing concentration after complete reaction, extracting the reaction liquid, adjusting the pH (potential of hydrogen) of an aqueous phase to be 4-5, filtering the aqueous phase and taking solid to obtain a compound 3; (3) dissolving the compound 3 in alcohol, adding palladium carbon catalysts, leading in hydrogen, performing reaction for 6-10 hours, filtering the solution after complete reaction, and concentrating and recrystallizing filtrate. The synthesis method has the advantages that the raw materials are easily obtained, reaction conditions are mild, yield is high, production is easily amplified, and cost can be reduced.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for the synthesis and preparation of unnatural tryptophan derivatives. Background technique [0002] Tryptophan has a wide range of uses in medicine, food, feed and so on. L-tryptophan is an essential amino acid for the human body, and its physiological role in the human body has long been known. Due to its remarkable physiological properties, D-tryptophan is used to synthesize a variety of polypeptide drugs, and it is playing an increasingly important role in medicine. [0003] There are many synthetic methods of tryptophan and its derivatives, mainly starting from indole, passing through 3-indole aldehyde, and then condensing with hippuric acid, hydantoin, thiohydantoin and other substances; Reduction, hydrolysis to get tryptophan. Another synthetic method is to condense Phyllanthine with amino or nitro-substituted malonate, and the condensate is decarboxylated, red...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/20
CPCC07D209/20
Inventor 张锐豪黄良富李新玲金灿李竞宇
Owner 上海毕得医药科技股份有限公司
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