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Compound for preparation of 4 - (10 B) dihydroxy boryl- L - phenylalanine

A technology of phenylalanine and hydroxyboron, which is applied in the field of compounds used to prepare 4-(10B) dihydroxyboron-L-phenylalanine, and can solve problems such as difficulty in preparation, inability to apply to preparation, etc.

Inactive Publication Date: 2015-03-25
TAIWAN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In view of prior art preparation 4-( 10 B) Dihydroxyboryl-L-phenylalanine faces preparation difficulties and needs to undergo hydrogenation to obtain L- 10 Shortcomings such as BPA cannot be applied to the preparation of rich 10 The problem of the L-BPA of boron, one of the purposes of the present invention is to provide a kind of compound, it can prepare L- 10 BPA

Method used

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  • Compound for preparation of 4 - (10 B) dihydroxy boryl- L - phenylalanine
  • Compound for preparation of 4 - (10 B) dihydroxy boryl- L - phenylalanine
  • Compound for preparation of 4 - (10 B) dihydroxy boryl- L - phenylalanine

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Embodiment 1

[0018] (1) Prepare (S)-N-tert-butoxycarbonyl- 4-( 10 B) Dihydroxyboryl phenylalanine

[0019]

[0020]

[0021] First, a 3-liter three-necked bottle equipped with a mechanical stirrer, a thermometer, and a nitrogen inlet joint sealed with a rubber gasket was prepared. Inject 750 milliliters of 2-methyltetrahydrofuran into the three-necked flask, then add 128 millimoles (50.0 grams, 100% purity) of (S)-N-tert-butoxycarbonyl-4-iodophenylalanine, And the two were uniformly stirred to form a solution; after that, 393 mmol (90.1 g, 106 ml) of 10 Tributyl borate was added to the solution to form a mixed solution.

[0022] Next, the mixed solution was cooled to between -85°C and -76°C, and a 1.6M (600 mmol, 375 ml) hexane solution of n-butyllithium (n-butyllithium) was added dropwise to the mixture over 3 hours. Mix the solutions to obtain a reaction mixture.

[0023] Then, the reaction mixture was stirred at -80°C for 0.5 hours, and a small amount of the reaction mixture ...

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Abstract

The invention relates to a compound for preparation of 4 - (10 B) dihydroxy boryl- L - phenylalanine, the compound has the structure as shown in formula (I), wherein R represents a protective group, the protective group is selected from a group consisting of t-butyloxycarboryl, triphenylmethyl, 3, 5 - dimethoxy phenyl isopropyloxy carbonyl, 2 - (4 - biphenylyl) isopropyloxy carbonyl and 2-nitro phenyl sulfinyl, the compound 10 boron purity is greater than or equal to 98%, and the enantiomeric excess is greater than or equal to 99%.

Description

technical field [0001] The present invention relates to a method for preparing 4-( 10 B) dihydroxyboryl-L-phenylalanine (4-( 10 B) borono-L-phenylalanine, L- 10 BPA), especially a compound for the preparation of L- with high isotopic purity and high optical purity 10 Compounds of BPA. Background technique [0002] 4-Dihydroxyboryl-L-phenylalanine (4-borono-L-phenylalanine, L-BPA) is an important boron compound known to be able to treat cancer with boron neutron capture therapy (BNCT) ; and contains 10 Boron 4-( 10 B) dihydroxyboryl-L-type phenylalanine (4-( 10 B) borono-L-phenylalanine, L- 10 BPA) is a key factor accumulated in tumor cells. It can then use thermal neutron beams to irradiate boron elements accumulated in tumor cells to kill tumor cells by capturing high-energy particles generated by the reaction, thereby achieving the goal of treating cancer. Purpose. therefore, 10 Boron can promote L- 10 BPA has emerged as a treatment for cancer through boron neut...

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCY02P20/55C07F5/025
Inventor 许坤旺黄淑芬萧家政
Owner TAIWAN BIOTECH