Synthetic methods of F-BPA and F-BPA intermediates, intermediates and application of intermediates

A technology of F-BPA and intermediates, applied in the field of F-BPA nucleophilic fluorination synthesis, can solve the problems of high manufacturing cost, low specific activity, and products with carriers, etc.

Active Publication Date: 2018-07-20
CHINA INSTITUTE OF ATOMIC ENERGY
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to solve the problems that the F-BPA produced by the electrophilic fluorination method of BPA has a carrier, low specific activity, high manufacturing cost, etc., the invention provides a F-BPA nucleophilic fluorination synthesis method and intermediate synthesis Methods, intermediates and their applications

Method used

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  • Synthetic methods of F-BPA and F-BPA intermediates, intermediates and application of intermediates
  • Synthetic methods of F-BPA and F-BPA intermediates, intermediates and application of intermediates
  • Synthetic methods of F-BPA and F-BPA intermediates, intermediates and application of intermediates

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preparation example Construction

[0066] According to one embodiment of the present invention, a kind of F-BPA nucleophilic fluorination synthetic method is provided, and the method comprises the following steps:

[0067] (1) Synthesis of compound 2

[0068] Add compound 1 and dimethylammonium hydrochloride to a solvent mixed with dimethyl sulfoxide and water, and add K in more than 2 times 2 CO 3 , heated to reflux for 6h to 36h; wherein, compound 1: dimethylammonium hydrochloride: K 2 CO 3 The molar ratio is 1:1-5:1-5; the reaction and the structural formula of the compound 1 are shown in the reaction formula 1; after the reaction is completed, the compound 2 is obtained by separation and purification.

[0069]

[0070] (2) Synthesis of compound 3

[0071] Under the protection of an inert gas, mix the dichloromethane solution of compound 2 with the dichloromethane solution of methyl-trifluoromethanesulfonate, and stir for 3h to 12h, wherein, compound 2: methyl-trifluoromethane The molar ratio of sulf...

Embodiment 1

[0121] This embodiment relates to the nucleophilic fluorination synthesis of F-BPA, and the synthesis process includes the following steps:

[0122] (1) Synthesis of compound 2

[0123] Add 0.84g compound 1, 0.82g dimethyl ammonium hydrochloride, 0.83g K 2 CO 3 , add a reaction solvent composed of 20mL dimethyl sulfoxide and 8mL water, reflux for 2h, add 0.55g K to the side port 2 CO 3 , continue the reflux reaction for 4h, lower the reaction solution to room temperature, stop the reaction, add the reaction solution to 40mL saturated K 2 CO 3 In the aqueous solution, the reaction solution is divided into two layers, separated by a separatory funnel with K 2 CO 3 The remaining reaction solution was extracted twice with 30 mL of diethyl ether, the diethyl ether layers were combined, washed once with 30 mL of water, and dried overnight with anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration, diethyl ether was rotary evaporated to dryness to ...

Embodiment 2

[0133] This example involves 18 The nucleophilic fluorination of F-BPA is synthesized, and the synthesis process includes the following steps:

[0134] (1) Synthesis of compound 2

[0135] Add 0.84g compound 1, 0.82g dimethyl ammonium hydrochloride, 0.83g K 2 CO 3 , add a reaction solvent composed of 20mL dimethyl sulfoxide and 8mL water, reflux for 2h, add 0.55g K to the side port 2 CO 3 , continue the reflux reaction for 4h, the reaction solution is lowered to room temperature, and the reaction is stopped, and the reaction solution is added to 40mL saturated K 2 CO 3 In the aqueous solution, the reaction solution is divided into two layers, separated by a separatory funnel with K 2 CO 3 The remaining reaction solution was extracted twice with 30 mL of diethyl ether, the diethyl ether layers were combined, washed once with 30 mL of water, and dried overnight with anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration, diethyl ether was rota...

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Abstract

The invention provides a nucleophilic fluorination based synthetic method of F-BPA, a synthetic method of intermediates, the intermediates and an application of the intermediates. The nucleophilic fluorination based synthetic method of F-BPA comprises the following steps: 1, synthesizing a compound 2 from raw materials including a compound 1, dimethylamine hydrochloride and the like; 2, synthesizing a compound 3 from raw materials including the compound 2, methyl-trifluoromethanesulfonate and the like; 3, synthesizing a compound 4 from raw materials including the compound 3, K2.2.2 and the like; 4, synthesizing a compound 5 from raw materials including the compound 4, an NaBH4 aqueous solution, an HI aqueous solution and the like; 5, synthesizing the target product from raw materials including the compound 5, N-(diphenylmethyl)tert-butyl glycinate and the like under the catalytic action of an Maruoka chiral phase transfer catalyst.

Description

technical field [0001] The invention belongs to the field of radiopharmaceuticals, and in particular relates to a F-BPA nucleophilic fluorination synthesis method, an intermediate synthesis method, an intermediate and applications thereof. Background technique [0002] Boron neutron capture therapy (BNCT) is a dual radiotherapy method that uses 10 Drug B is introduced into the body through oral or injection methods, and makes it selectively gather in cancer cells, and then irradiates the lesion with neutrons to make it 10 B happens 10 B(n,α) 7 Li nuclear reaction, using the resulting alpha particles and 7 Li ions kill cancer cells at the cellular level. The first clinical trial of BNCT for human brain tumors began in the early 1950s. After decades of exploration, research and clinical trials, BNCT is considered to be an effective method for treating tumors (the treatment of superficial glioma The 5-year survival rate reaches 33.3%). Compared with the current methods of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07B59/00
CPCC07B59/001C07B2200/05C07F5/025
Inventor 罗志福李凤林樊彩云刘子华王跃
Owner CHINA INSTITUTE OF ATOMIC ENERGY
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