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Chiral phosphamide synthesizing method

A synthesis method and phosphoramide technology, which is applied in the field of synthesizing chiral phosphoramides with a single configuration of the phosphorus chiral center, can solve the problems of difficult operation and waste, and achieve the effects of easy acquisition, mild reaction conditions, and low raw material prices

Inactive Publication Date: 2009-06-03
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But this method is not easy to operate. Not every product can be disassembled, and half of the products are not in the configuration we need and will be discarded. The waste is serious.

Method used

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  • Chiral phosphamide synthesizing method
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Embodiment 1

[0021] In a 25mL round-bottomed flask, put 0.5mmol (Rp) menthoxyphenyl hydrogen phosphite and 30mg ammonia water in 10mL acetonitrile, keep the temperature at 0°C, and finally add 0.5mmol of C 2 Cl 6 Dissolve the solution in 5ml of acetonitrile and continue to stir overnight. After the reaction is over, remove the solvent under reduced pressure to obtain a crude product. Purification by column chromatography was carried out under the condition of eluent whose polarity was petroleum ether: ethyl acetate = 5:1-1:2 to obtain the product with a yield of 75%.

Embodiment 2

[0023] In a 25mL round-bottomed flask, dissolve 0.5mmol (Rp) menthyl isopropoxyhydrogen phosphite and 1mmol phenylalanine in 5mL of water, add 5mL of acetonitrile, keep the temperature within 8°C, and then add Add 1 equivalent of triethylamine, and finally add 20 mmol of CCl dropwise 4 , continue to stir overnight, after the reaction is over, remove acetonitrile and other low-boiling organic matter under reduced pressure, remove unreacted menthyl isopropoxyhydrogen phosphite with 10 mL of dichloromethane, and use 1mol.L -1 dilute hydrochloric acid to adjust the pH value to about 3, dichloromethane 10mL extraction to obtain the crude product, the polarity of petroleum ether: ethyl acetate = 5:1 ~ 1:2 eluent conditions for column chromatography separation and purification, The product was obtained with a yield of 70%.

Embodiment 3

[0025] In a 25mL round bottom flask, 0.5mmol (Rp) menthoxybutoxyhydrogen phosphite and 1mmol diethylamine were dissolved in 10mL dichloromethane, the temperature was kept at -40°C, and then 1 equivalent of tris Ethylamine, finally dropwise the dichloromethane solution of the diisopropylamino chloride of 1mmol, react 3 hours after completion of dropwise addition, after reaction finishes, remove low-boiling point organic matter under reduced pressure, at polarity is sherwood oil: ethyl acetate= Purification by column chromatography was carried out under the condition of 5:1-1:2 eluent to obtain the product with a yield of 70%.

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Abstract

The invention discloses a chiral phosphamide synthesizing method, relating to a chiral phosphamide, in particular to a method for synthesizing chiral phosphamide in which phosphorus has single chiral center configuration. The invention provides the chiral phosphamide synthesizing method which has the advantages of low-price and easily obtained raw materials, high productivity, no easy racemization, simple operation and is suitable for large-scale production. Under the existence of halogenating agents and organic base, the chiral phosphamide, in which phosphorus has single chiral center configuration, or phosphinate and unhindered amina, primary amine or secondary amine reacts in a solvent to generate corresponding chiral phosphamide in which phosphorus has single chiral center configuration.

Description

technical field [0001] The present invention relates to a chiral phosphoramide, in particular to a method for synthesizing a chiral phosphoramide with a single configuration of the phosphorus chiral center, which comprises making the phosphorus chiral Chiral hydrogen phosphite (phosphonite) ester with a single configuration of the sex center reacts with amine compounds in a solvent. More specifically, the method uses hexachloroethane, etc. as a halogenating agent, and triethylamine as a catalyst and an acid-binding agent, so that chiral hydrogen phosphite (phosphine) ester and free ammonia, primary amine or secondary amine Reaction in a solvent generates a chiral phosphoramide with a single configuration of the phosphorus chiral center. Background technique [0002] Phosphoramides have a variety of important uses in medicine, such as being used as prodrugs to help drugs enter the cell membrane, and then taking off the phosphoryl group to release the original drug; directly ...

Claims

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Application Information

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IPC IPC(8): C07F9/24C07F9/36C07F9/44
Inventor 赵玉芬王刚唐果许鹏翔韩立彪
Owner XIAMEN UNIV
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