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Preparation method of tris (2-carboxyethyl) phosphine hydrochloride

A technology of phosphorus hydrochloride and carbonyl ethyl, which is applied in the field of preparation of triphosphorus hydrochloride, can solve the problems of low product purity and inability to achieve effective separation, and achieve high product purity, strong route feasibility, and low toxicity of raw materials Effect

Active Publication Date: 2013-08-07
SUZHOU HIGHFINE BIOTECH
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  • Summary
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

This route uses four hydroxymethyl phosphorus chloride to replace the highly toxic gas phosphine to synthesize tricyanoethyl phosphorus, but tricyanoethyl phosphoric acid hydrolysis gives tris (2-carbonyl ethyl) phosphorus hydrochloride (TCEP hydrochloride) and ammonium chloride solid mixture, the two salt mixtures cannot be effectively separated, and the product purity is low

Method used

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  • Preparation method of tris (2-carboxyethyl) phosphine hydrochloride
  • Preparation method of tris (2-carboxyethyl) phosphine hydrochloride
  • Preparation method of tris (2-carboxyethyl) phosphine hydrochloride

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Embodiment 1

[0030] 1.1 Preparation of compound trimethyl 3, 3', 3''-phosphinetriyltripropionate

[0031] Under the condition of mechanical stirring, add tetrakis hydroxymethyl phosphorus chloride aqueous solution (71.2g, 0.30mol) and ethanol (75ml) with a mass fraction of 80% to a 250ml reaction flask, cool with ice water and protect with nitrogen, add hydroxide Potassium (16.8g, 0.30mol) was dissolved in 23ml of ice water, and the temperature rose slightly; then ethyl acrylate (90g, 0.9mol) was added dropwise, and the temperature was controlled at 35-40°C, a large amount of solids were formed, keep stirring after dropping 4 hours. Pour 300ml of ice water into the reaction solution, stir and filter with suction, wash the filter cake with ice water, and dry it with suction to obtain 88g of white solid (that is, the compound trimethyl 3, 3', 3''-phosphinetriyltri propionate), yield 86.6%, for the next step reaction. The NMR data of the resulting product are as follows:

[0032] 1 ...

Embodiment 2

[0037] 2.1 Preparation of compound trimethyl 3, 3', 3''-phosphinetriyltripropionate

[0038] Under the condition of mechanical stirring, add tetrakis hydroxymethyl phosphorus chloride aqueous solution (71.2g, 0.30mol) and tetrahydrofuran (75ml) with a mass fraction of 80% into a 250ml reaction flask, cool with ice water and protect with nitrogen, add sodium hydroxide (12g, 0.30mol) dissolved in 23ml of ice water solution, the temperature rose slightly. Then ethyl acrylate (126g, 1.26mol) was added dropwise, and the temperature was controlled at 55-60°C. A large amount of solids were formed, and the mixture was kept stirring for 6 hours after dropping. Pour 300ml of ice water into the reaction solution, stir and filter with suction, wash the filter cake with ice water, and dry it with suction to obtain 94g of white solid, (that is, the compound trimethyl 3, 3', 3''-phosphine triyl Tripropionate), yield 92.5%, is used for next step reaction. The NMR data of the resulting p...

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Abstract

The invention provides a preparation method of tris (2-carboxyethyl) phosphine hydrochloride. The preparation method comprises the following steps of: (a) carrying out an alkylation reaction on tetrakisphosphonium chloride and a compound (I) in a formula in the presence of an organic solvent to obtain a compound (II) in the formula, wherein the alkylation reaction temperature is 30-60 DEG C; and (b) carrying out a hydrolysis reaction on the compound (II), obtained in the step (a), in the formula to obtain a compound III, namely the tris (2-carboxyethyl) phosphine hydrochloride. The preparation method provided by the invention is simple and convenient to operate, low in cost, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to the field of compound preparation, more particularly to a preparation method of tris(2-carbonylethyl)phosphorus hydrochloride. Background technique [0002] Tris(2-carbonylethyl)phosphate hydrochloride (TCEP hydrochloride) is a new type of reducing and deprotecting agent for thiolated DNA. Thiolated DNA terminal sulfur atoms tend to form dimers in solution, especially in the presence of oxygen. This dimerization greatly reduces the efficiency of some coupling reaction experiments (such as the immobilization of DNA in biosensors); while adding tris (2-carbonylethyl) phosphate hydrochloride (TCEP hydrochloride) to the DNA solution ), removed after a period of reaction, can reduce the dimerization of DNA. Tris (2-carbonylethyl) phosphate hydrochloride (TCEP hydrochloride) is also often used for the reduction of disulfide bonds in proteins, which can be used to prevent intramolecular or Intermolecular disulfide bonds. Tris(2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50
Inventor 蒋兆芹吕敏杰孙豪义
Owner SUZHOU HIGHFINE BIOTECH
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