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Method for synthesizing 4-dihydroxyborane-2-fluorophenylalanine

A technology of fluorophenylalanine and dihydroxyborane, applied in the field of synthesis of 4-dihydroxyborane-2-fluorophenylalanine, achieving high yield, easy purification, and simple synthesis steps

Active Publication Date: 2013-01-23
NANJING PET TRACER +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to solve the technical problem that the existing 4-dihydroxyborane-2-fluorophenylalanine needs to be reacted with fluorine in special equipment when synthesizing, and to provide a synthetic 4- Dihydroxyborane-2-fluorophenylalanine method

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  • Method for synthesizing 4-dihydroxyborane-2-fluorophenylalanine

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Embodiment Construction

[0027] The present invention is described in further detail below in conjunction with embodiment.

[0028] Nitration reaction: Dissolve 6.63g of p-iodotoluene (1) in 5mL of acetic anhydride, control the temperature at 0°C, stir magnetically, slowly add concentrated 3mL of HNO 3 After the addition, the temperature was controlled to 20-25°C, reacted for 4 hours, cooled to room temperature, and added NaOH solution to adjust the pH to 7, the mixture was extracted 3 times with 200 mL of ethyl acetate, washed with saturated brine, and the organic phase was washed with anhydrous Na 2 SO 4 Dry, mix the sample with silica gel, petroleum ether: ethyl acetate (v:v) = 1:3-1:5 as the mobile phase to pass through the column, and rotary evaporate at 25°C to obtain 2.80 g of p-iodo-o-nitrotoluene (2) as a yellow oil , the yield is 35%.

[0029] Bromination reaction: Dissolve 2.63 g of p-iodo-o-nitrotoluene (2) in 50 mL of carbon tetrachloride, then add 1.78 g of N-bromosuccinimide (NBS) and...

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Abstract

The invention discloses a method for synthesizing a 4-dihydroxyborane-2-fluorophenylalanine, wherein the method comprises the following steps of taking p-iodotoluene as a raw material, carrying out nitratlon reaction and bromination reaction in sequence on the raw material to obtain p-iodo-o-nitrobenzyl bromine, firstly substituting the p-iodo-o-nitrobenzyl bromine with diethyl sodium acetamidomalonate to obtain diethyl 2-acetamido-2-(4-iodo-2-nitrobenzyl) malonate, and then reacting with ammonium tetrabutyl fluoride to obtain fluorinated diethyl 2-acetamido-2-(4-iodo-2-fluorobenzyl) malonate, carrying out Suzuki coupling reaction on the obtained fluorinated product and bisdiboron under an inert atmosphere, hydrolyzing the obtained diethyl 2-acetamido-2-(4-valerylboron-2-fluorobenzyl) malonate to obtain the 4-dihydroxyborane-2-fluorophenylalanine. The method provided by the invention is not necessary to use fluorine gas; the method provided by the invention has low requirement to production equipment; the reaction is carried out under common experimental conditions; the method provided by the invention has the advantages of simple synthesis step, high yield, high product purity and easy purification.

Description

technical field [0001] The invention relates to a synthesis method of 4-dihydroxyborane-2-fluorophenylalanine used in the field of boron neutron capture therapy (BNCT). Background technique [0002] Traditional brain tumor treatment methods cannot completely kill tumor cells, while boron neutron capture therapy (BNCT) is a promising method to cure glioma, but due to the existence of the blood-brain barrier, many boron-containing drugs are prevented from entering brain, so how to deliver sufficient doses of 10 B is the key to the successful application of BNCT. [0003] According to the faster replication rate of solid tumor cells with higher metabolism, it synthesizes specific boron-containing compounds and selectively accumulates in tumor cells. Boron p-dihydroxyphenylalanine (BPA) has been used in boron neutron capture therapy (BNCT) since 1987 because of its enrichment properties in tumors. It is a 10 B-labeled biomolecular analogs that can enter tumor cells through me...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 徐建锋虞善友李新平李桺方久利陆铖刘强
Owner NANJING PET TRACER
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