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Method for preparing ubenimex hydrolysis intermediates

A technology of Ubenimex and intermediates, which is applied in the field of preparation of Ubenimex hydrolysis intermediates, can solve the problems of wasting solvents, high energy consumption, and not suitable for large-scale production, and achieve energy saving, high yield, and Effect of saving solvent and energy

Inactive Publication Date: 2012-06-13
深圳万乐药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process of this method will remove the resolving agent and hydrolyze step by step, use ethyl acetate to extract three times, and concentrate the aqueous solution twice under reduced pressure, which wastes solvent and consumes a lot of energy, and is not suitable for large-scale production

Method used

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  • Method for preparing ubenimex hydrolysis intermediates
  • Method for preparing ubenimex hydrolysis intermediates
  • Method for preparing ubenimex hydrolysis intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Put 200g of (2S, 3R)-3-acetamido-2-hydroxy-4-phenylbutyric acid S(-)-α-phenethylamine salt into the reactor, add 640g of 4N hydrochloric acid aqueous solution, at 50°C Stir for 3 hours, add 4N sodium hydroxide solution to adjust pH=8.2, and filter with suction to obtain 109.6 g of crude product. The crude product was heated to 90°C with 986.4g of 60% DMF-water solution to dissolve, stirred and crystallized at room temperature, filtered with suction, and dried to obtain 103.63g of white crystals with a purity of 98.6% and an optical rotation of +31.7° (C=1, 1N HCl ), yield 93.27%.

Embodiment 2

[0027] Put 200g of (2S, 3R)-3-acetamido-2-hydroxy-4-phenylbutyric acid S(-)-α-phenethylamine salt into the reactor, add 640g of 4N aqueous hydrochloric acid, at 70°C Stir for 3 hours, add 6N sodium hydroxide solution to adjust pH=8.2, and filter with suction to obtain 110.1 g of crude product. The crude product was heated to 90°C with 990.9g of 60% DMF-water solution to dissolve, stirred and crystallized at room temperature, filtered with suction, and dried to obtain 102.98g of white crystals with a purity of 98.5% and an optical rotation of +31.5° (C=1, 1N HCl), yield 92.87%.

Embodiment 3

[0029] Put 200g of (2S, 3R)-3-acetamido-2-hydroxy-4-phenylbutyric acid S(-)-α-phenethylamine salt into the reactor, add 1000g of 4N hydrochloric acid aqueous solution, at 60°C Stir for 3 hours, add 6N sodium hydroxide solution to adjust pH=8.2, and filter with suction to obtain 105.4 g of crude product. The crude product was heated to 90°C with 700g of 70% DMF-water solution to dissolve, stirred and crystallized at room temperature, suction filtered, and dried to obtain 103.50g of white crystals with a purity of 98.2% and an optical rotation of +31.4° (C=1, 1N HCl ), yield 93.21%.

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Abstract

The invention provides a method for preparing ubenimex hydrolysis intermediates (2S and 3R)-3-amino-2-hydroxyl-4-phenylbutyric acid. A method that a potential of hydrogen (pH) value is adjusted after hydrolysis is directly utilized to dissociate a resolving agent, hydrochloric acid solution with proper concentration and volume is selected to perform the hydrolysis, thereby enabling operation to be suitable for industrialization production and achieving ideal yield and purity. By utilizing dimethyl formamide (DMF) solvent crystallization, product quality is further improved and white crystals with high purity and optical activity are produced. The method is simple and convenient to operate, saved in solvents and energy sources, high in yield and suitable for the industrialization production.

Description

technical field [0001] The invention relates to the field of organic chemistry, and further relates to a preparation method of an ubenimex hydrolysis intermediate. Background technique [0002] Ubenimex (foreign name Ubenimex, Bestalin) is a dipeptide compound isolated from the culture fluid of Streptomyces ofivorecticuli, which can competitively inhibit aminopeptidase B (aminopeptidase B) and leucine peptidase (Leucineamino Peptidase) and caspase (Caspase), enhance the function of T cells, enhance the killing activity of NK cells, and increase the synthesis of colony-stimulating factor to stimulate the regeneration and differentiation of bone marrow cells. It can interfere with the metabolism of tumor cells, inhibit tumor cell proliferation, cause tumor cell apoptosis, activate human cellular immune function, stimulate the production and secretion of cytokines, and promote the production and proliferation of anti-tumor effector cells. It can be used in conjunction with che...

Claims

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Application Information

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IPC IPC(8): C07C229/34C07C227/20C07C227/42
Inventor 陈轶之张广明钱建彬钱怀伟
Owner 深圳万乐药业有限公司
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