Synthetic method of 2-dipalmitoyl-sn-glycero-3-phosphoethanolamine

A technology of dipalmitoylphosphatidylethanolamine and its synthesis method, which is applied in the direction of phosphorus organic compounds, etc., and can solve the problems of many impurities, unsuitable for large-scale industrial production, and long reaction time.

Inactive Publication Date: 2013-05-08
深圳万乐药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] It is found in the research that the reaction is carried out according to the method disclosed in the literature, the reaction time is long, the impurities are more, the post-treatment of compound II is complicated, and it is not suitable for large-scale industrial production

Method used

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  • Synthetic method of 2-dipalmitoyl-sn-glycero-3-phosphoethanolamine
  • Synthetic method of 2-dipalmitoyl-sn-glycero-3-phosphoethanolamine
  • Synthetic method of 2-dipalmitoyl-sn-glycero-3-phosphoethanolamine

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Embodiment 1

[0021] Synthesis of Intermediate II

[0022] Add compound III (28.2 g, 0.09 mol) into the reactor, add anhydrous tetrahydrofuran (80 ml), stir and dissolve, and set aside. Take another reactor, add compound IV (40g, 0.07mol) and molecular sieve-dried pyridine (200ml), heat to 40°C to dissolve it completely, and cool to room temperature. The solution of compound IV was added dropwise to the standby solution in a cold bath at 8°C, and the reaction was continued at 10°C for 35 minutes after the drop was completed, and the reaction was completed. Add 6N hydrochloric acid dropwise at 10°C to adjust the pH to 1-2, stir for 3 minutes after the dropwise addition, and stand for 3 hours for crystallization. Filter, add water to the filter cake and stir wash it once, filter, and oven dry at 40°C to obtain 49.8g of intermediate II, with a purity of 93.9% and a yield of 86.2%.

[0023] Synthesis of dipalmitoylphosphatidylethanolamine

[0024] Intermediate II (49.8g) was added into the r...

Embodiment 2

[0026] Synthesis of Intermediate II

[0027] Add compound III (140 g, 0.454 mol) into the reactor, add anhydrous tetrahydrofuran (400 ml), stir to dissolve, and set aside. Take another reactor, add compound IV (200g, 0.35mol) and molecular sieve-dried pyridine (800ml), heat to 40°C to make it fully dissolved, and cool to room temperature. The solution of compound IV was added dropwise to the standby solution in a cold bath at 10°C, and the reaction was continued at 10°C for 70 minutes after dropping, and the reaction was completed. Add 6N hydrochloric acid dropwise at 10°C to adjust the pH to 1-2, stir for 3 minutes after the dropwise addition, and stand for 2 hours for crystallization. Filtrate, add water to the filter cake and stir wash once, filter, and oven-dry at 40°C to obtain 252.9 g of Intermediate II with a purity of 95.1% and a yield of 87.5%.

[0028] Synthesis of dipalmitoylphosphatidylethanolamine

[0029] Add intermediate II to the reactor, add tetrahydrofuran...

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Abstract

The invention provides a synthetic method of 2-dipalmitoyl-sn-glycero-3-phosphoethanolamine. The method comprises the steps of taking 2-phthalimide-phosphorodichloridate, and alpha, beta-glycerol-1,3-dipalmitate as materials; respectively dissolving by tetrahydrofuran and pyridine; taking the pyridine as alkali to carry out hydrolysis reaction during condensation reaction; directly filtering to obtain pure intermediate compound II; taking the tetrahydrofuran and ethanol as solvents, and carrying out deprotection by hydrazine hydrate to obtain the 2-dipalmitoyl-sn-glycero-3-phosphoethanolamine. The method is simple and convenient to operate, rapid to react, and suitable for industrial production; and a reagent is saved.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and further relates to a method for synthesizing dipalmitoylphosphatidylethanolamine, an intermediate of michalum peptide. Background technique [0002] Miphatide liposome injection is a product of IDM Pharmaceutical Company (trade name: Mepact), which is used for the treatment of non-metastatic, resectable osteosarcoma. Drug fut1989, 14, (3): 220 discloses a synthetic method of michalum peptide, wherein the last step of the synthetic route uses dipalmitoylphosphatidylethanolamine as a synthetic intermediate. [0003] Dipalmitoylphosphatidylethanolamine (compound of formula I) has the following structural formula: [0004] [0005] Molecular formula: C37H74NO8P [0006] CAS: 923-61-5 [0007] Dipalmitoyl phosphatidylethanolamine is not only an important intermediate in the synthesis of miphatide, but also proven to be effective in the treatment of senile mental decline, genetic and non-here...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09
Inventor 钱建彬陈齐阳李昌希李萍柏江涛张广明
Owner 深圳万乐药业有限公司
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