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Synthetic method for N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride

A technology of glycine methyl ester and synthesis method, which is applied in the field of chemical synthesis of intermediates, can solve problems such as difficult operation, high cost, and low yield, and achieve the effects of reducing usage, simple operation, and cost reduction

Active Publication Date: 2014-12-17
SUZHOU VIVOTIDE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Technical problem to be solved: the object of the present invention is to overcome the above problems existing in the prior art, provide a new method to synthesize N-(2-Fmoc-aminoethyl) glycine methyl ester hydrochloride, and solve the operation that the original similar synthetic method exists Difficult, low yield, high cost technical problems

Method used

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  • Synthetic method for N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride
  • Synthetic method for N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride
  • Synthetic method for N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride

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Embodiment 1

[0016] 1 Synthesis of Wt13003Fa:

[0017]

[0018] At room temperature, chloroacetic acid (800g, 8.47 mol) was added to ethylenediamine (5.5 L ) in batches within three hours, and the stirring was completed overnight, and the excess ethylenediamine was distilled off with an oil pump under reduced pressure to obtain a light yellow The viscous oil was added with DMSO overnight, a white solid precipitated out, filtered, washed twice, and dried to obtain 700 g of crude product (yield: 54.5%, purity 60% as determined by TLC), which was directly used in the next step.

[0019] 2 Synthesis of Wt13003Fb2:

[0020]

[0021] WT13003Fa (75g, 0.64 mol) was suspended in methanol (1.5L), cooled to 0°C, added dropwise with thionyl chloride (230 mL, 3.2mol), and heated to reflux for 4 hours, and the solvent was removed under reduced pressure with a water pump to obtain white The product (84g, yield 100%) was directly used in the next step.

[0022] 3 Synthesis of Wt13003Fc:

[0023] ...

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Abstract

A disclosed synthetic method for N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride comprises the following steps: reacting ethylenediamine with a halogenated acetic acid, using DMSO for recrystalization and further for obtaining N-(2-aminoethyl)glycine (WT13003Fa); taking N-(2-aminoethyl)glycine as a raw material, reacting with methanol with the participation of thionyl chloride , so as to prepare N-(2-aminoethyl)glycine methyl ester (WT13003Fb2); and then reacting N-(2-aminoethyl)glycine methyl ester with Fmoc-osu to prepare N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride (WT13003Fc). The N-(2-Fmoc-aminoethyl)glycine methyl ester hydrochloride prepared by employing the synthetic method has the purity of 97% and the yield of 47%.

Description

technical field [0001] The invention belongs to the field of chemical synthesis of intermediates, and relates to a chemical synthesis method of intermediates, 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 current mainstream synthesis steps of N-2-(aminoethyl)-glycine are as follows: a. at room temperature, add chloroacetic acid to ethylenediamine, complete stirring overnight, and remove excess ethylenediamine by distillation under reduced pressure to obtain light The yellow viscous oil was dissolved by adding DMSO, and a white solid precipitated overnight, filtered, washed twice with DMSO, and dried to obtain the crude product N-(2-aminoethyl)glycine, which was directly used in the next step. b. Suspend N-(2-aminoethyl)glycine in dichloromethane DMF, add trimethylchlorosilane, stir at room temperature...

Claims

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Application Information

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IPC IPC(8): C07C269/04C07C271/20
CPCY02P20/55
Inventor 卢俊灵
Owner SUZHOU VIVOTIDE BIOTECH
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