Synthesis method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride

The technology of a glycine methyl ester and a synthetic method is applied in the synthesis field of N-glycine methyl ester hydrochloride, and can solve the problems of high cost and low yield, and achieve the effects of reducing usage, reducing cost and simple operation.

Inactive Publication Date: 2018-08-21
苏州凌科特新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved: in order to solve the above-mentioned technical problem, the inventive method solves the low production rate of the preparation method in the prior art, the technical problem that the cost is high, Fmoc-osu is added dropwise to N-(2-aminoethyl) glycine methyl In the mixed solution of ester, alkali and organic solvent, the yield of the product can be greatly increased, as high as 81%, and its purity is as high as 98%.

Method used

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  • Synthesis method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride

Examples

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Effect test

Embodiment 1

[0020] A kind of synthetic method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride, comprises the following steps:

[0021] The first step: at room temperature, add chloroacetic acid (800g, 8.47 mol) to ethylenediamine (5.5 L ) in batches within 3 hours, stir overnight after completion, and remove excess ethylenediamine by distillation under reduced pressure with an oil pump to obtain light Yellow viscous oil, dimethyl sulfoxide was added overnight, a white solid was precipitated, filtered, washed twice, and dried to obtain 700g of crude product N-(2-aminoethyl)glycine, yield: 54.5%, measured by TLC Purity is 60%, directly used in the next step;

[0022] Step 2: Suspend N-(2-aminoethyl)glycine in methanol (1.5L), cool to 0°C, add thionyl chloride (230mL, 3.2mol) dropwise, heat to reflux for 4h after completion, and use a water pump The solvent was removed under reduced pressure to obtain 84 g of white product N-(2-aminoethyl) glycine methyl ester, yield: 100%, whic...

Embodiment 2

[0025] A kind of synthetic method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride, comprises the following steps:

[0026] The first step: at room temperature, add chloroacetic acid (800g, 8.47 mol) to ethylenediamine (5.5 L ) in batches within 3 hours, stir overnight after completion, and remove excess ethylenediamine by distillation under reduced pressure with an oil pump to obtain light Yellow viscous oil, dimethyl sulfoxide was added overnight, a white solid was precipitated, filtered, washed twice, and dried to obtain 700g of crude product N-(2-aminoethyl)glycine, yield: 54.5%, measured by TLC Purity is 60%, directly used in the next step;

[0027] Step 2: Suspend N-(2-aminoethyl)glycine in methanol (1.5L), cool to 0°C, add thionyl chloride (230mL, 3.2mol) dropwise, heat to reflux for 4h after completion, and use a water pump The solvent was removed under reduced pressure to obtain 84 g of white product N-(2-aminoethyl) glycine methyl ester, yield: 100%, whic...

Embodiment 3

[0030] A kind of synthetic method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride, comprises the following steps:

[0031] The first step: at room temperature, add chloroacetic acid (800g, 8.47 mol) to ethylenediamine (5.5 L ) in batches within 3 hours, stir overnight after completion, and remove excess ethylenediamine by distillation under reduced pressure with an oil pump to obtain light Yellow viscous oil, dimethyl sulfoxide was added overnight, a white solid was precipitated, filtered, washed twice, and dried to obtain 700g of crude product N-(2-aminoethyl)glycine, yield: 54.5%, measured by TLC Purity is 60%, directly used in the next step;

[0032] Step 2: Suspend N-(2-aminoethyl)glycine in methanol (1.5L), cool to 0°C, add thionyl chloride (230mL, 3.2mol) dropwise, heat to reflux for 4h after completion, and use a water pump The solvent was removed under reduced pressure to obtain 84 g of white product N-(2-aminoethyl) glycine methyl ester, yield: 100%, whic...

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Abstract

The invention provides a synthesis method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride. The preparation method is as follows: firstly, reacting ethylenediamine with haloacetic acid, andthen, carrying out recrystallization by using dimethyl sulfoxide to obtain N-(2-aminoethyl) glycine; secondly, mixing N-(2-aminoethyl) glycine with methanol, carrying out a reaction under the participation of thionyl chloride to prepare N-(2-aminoethyl) glycine methyl ester; and thirdly, mixing N-(2-aminoethyl) glycine methyl ester with an organic solvent and alkali, slowly dropwise adding Fmoc-osu, and adding a hydrochloric acid solution after ending the reaction to obtain N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride. By using the synthesis method of N-(2-Fmoc-aminoethyl) glycinemethyl ester hydrochloride, provided by the invention, the yield of the product can be greatly increased and reaches up to 81% or above, and the purity of the product reaches up to 98%.

Description

technical field [0001] The invention relates to the field of chemical synthesis methods, in particular to a synthesis method of N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride. Background technique [0002] N-2-(aminoethyl)-glycine is the alignment unit of the PNA (peptide nucleic acid) backbone. The mainstream synthetic steps of present N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride are as follows: a. at room temperature, chloroacetic acid is added in ethylenediamine, complete and stir overnight, and decompression distillation removes unnecessary Ethylenediamine, to obtain a light yellow viscous oil, add dimethyl sulfoxide to dissolve, a white solid precipitates overnight, filter, wash twice with dimethyl sulfoxide, and dry to obtain the crude product N-(2-aminoethyl) Glycine was used directly in the next step. b. Suspend N-(2-aminoethyl)glycine in dichloromethane DMF, add trimethylchlorosilane, stir at room temperature for 40 minutes, cool to 5°C, add ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/20
CPCC07C227/08C07C227/18C07C269/04C07C2603/18C07C271/20C07C229/16
Inventor 王鹤明
Owner 苏州凌科特新材料有限公司
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