Preparation method of N-Boc-1, 2-diaminoethane

A technology of diaminoethane and n-boc-1 is applied in the field of preparation of N-Boc-1,2-diaminoethane, can solve the problems of unsatisfactory cost and the like, and achieves low cost of raw materials, separation and purification operation Simple, high reaction conversion effect

Inactive Publication Date: 2018-10-23
湖南华腾制药有限公司
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Problems solved by technology

In addition Xu, Zhigang; DiCesare, John C.; Baures, Paul W. once proposed to prepare mono-protected ethylenediamine by removing the Cbz protecting group on N-Cbz-N'-Boc-ethylenediamine, although there is a high yield, but N-Cbz-N'-Boc-ethylenediamine must be prepared first, which is quite unsatisfactory in terms of cost

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  • Preparation method of N-Boc-1, 2-diaminoethane
  • Preparation method of N-Boc-1, 2-diaminoethane

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Embodiment Construction

[0016] N-Boc-1,2-diaminoethane

[0017] (1) Dissolve 160g (1.7mol, 1.0eq) of phenol in 1.1L of ethanol, add 258.3g (2.55mol, 1.5eq) of triethylamine and 20g (0.17mol, 0.1eq) of 4-dimethylaminopyridine. Cool the liquid nitrogen to -5-0°C, slowly add Boc2O ethanol solution (371.6g Boc2O dissolved in 150ml ethanol) dropwise, after the dropwise addition, naturally warm up to room temperature and stir for 1h, TLC detects that the phenol reaction is complete, stop the reaction. Concentrated to remove the solvent, separated and purified by column chromatography to obtain a light yellow liquid with a yield of 81.8%. The nuclear magnetic data are as follows: 1HNMR (400MHz, CDCl3): 1.4~1.51 (s, 9H); 7.26 (t, 1H); 7.29 (m, 2H) 7.42 (t, 2H).

[0018] (2) Dissolve 102.1g (1.7mol, 1.0eq) of ethylenediamine in ethanol, add tert-butyl phenyl carbonate (1.7mol, 1.0eq) dropwise under stirring at room temperature, and raise the temperature to 80°C for reflux reaction after the addition is compl...

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Abstract

The invention relates to a preparation method of N-Boc-1, 2-diaminoethane. The preparation method comprises 1) dissolving phenol, a catalyst and a base in a first organic solvent, and adding di-tert-butyl dicarbonate into the solution with the first solvent drop by drop for a reaction to obtain tert-butyl phenyl carbonate, and 2) dissolving 1, 2-diaminoethane in the first organic solvent, and adding tert-butyl phenyl carbonate into the solution drop by drop for a reaction to obtain a final product. The preparation method has simple separation and purification processes, has a small reaction temperature range and a high reaction yield and realizes a low raw material cost.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of N-Boc-1,2-diaminoethane. Background technique [0002] In the chemical synthesis of pharmaceutical intermediates, N-Boc-1,2-diaminoethane is widely used as a structural unit of bioconjugation chemistry. Especially such mono-protected ethylenediamine derivatives are often used to prepare pharmacologically active analogs and introduce ethylenediamine spacer arms. An ideal method for preparing such monoprotected ethylenediamine derivatives is particularly important. [0003] The traditional mono-Boc-protected ethylenediamine synthesis method is mainly to react quantitative Boc anhydride and ethylenediamine, and then purify qualified mono-Boc-protected ethylenediamine by column chromatography. However, the amount of Boc has a direct impact on the reaction conversion rate and yield. Improper control will cause the content of N-Boc-1,2-diaminoeth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C269/04C07C271/20
CPCC07C269/04C07C68/06C07C271/20C07C69/96
Inventor 陈芳军
Owner 湖南华腾制药有限公司
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