Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of synthesis technique of boc-1-amino-3,6-dioxa-1,8-octanediamine

A synthesis process and dioxa technology are applied in the preparation of carbamic acid derivatives, the preparation of organic compounds, organic chemistry and other directions, which can solve the problems of long steps, long process routes, and total yield of less than 50%, and reach the reaction time. The effect of short, simple reaction route and simple operation

Active Publication Date: 2021-03-09
暨明医药科技(苏州)有限公司
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, the document Preparation and biological assessment of hydroxycinnamic acidamides of polyamines. Fixon-Owoo, Solomon et al., Phytochemistry, 2003 (63), 315-334. That is to say, DODA is first put on trifluoroacetyl, then on Boc, and finally removes Synthesis of Boc-1-amino-3,6-dioxa-1,8-octanediamine by the method of trifluoroacetyl group, the method has long steps and the total yield is less than 50%
The process route is long and requires the use of dangerous azide compounds, which is not suitable for scale-up for industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthesis technique of boc-1-amino-3,6-dioxa-1,8-octanediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A kind of synthesis technique of Boc-1-amino-3,6-dioxa-1,8-octanediamine, it comprises the steps:

[0027] Add 148.2g DODA and 740mL acetonitrile into a 2L reaction flask, stir and lower the temperature to 0-5°C, dissolve 150.3g (1.1 equivalent) tert-butoxyyl chloride in 445mL toluene, and then control the temperature at 0-5°C. The toluene solution of tert-butoxyacyl chloride is slowly added dropwise to the acetonitrile solution of DODA, and the time of dropping is controlled within 1-2 hours. After the dropwise addition, stir for 30 minutes, filter, and filter the cake with a mixture of 70 mL of acetonitrile:toluene=5:3. Solvent rinsing, the filter cake after rinsing was dissolved in 1L of water, adjusted to pH 10 with sodium hydroxide solution, extracted twice with methyl tert-butyl ether, 750mL each time, combined organic phases, washed with 250mL of water, concentrated , and dried to obtain 183.7g of Boc-1-amino-3,6-dioxa-1,8-octanediamine with a purity of 99.3% and...

Embodiment 2

[0029] A kind of synthesis technique of Boc-1-amino-3,6-dioxa-1,8-octanediamine, it comprises the steps:

[0030] Add 148.2g DODA and 740mL acetonitrile into a 2L reaction flask, stir and cool down to 0-5°C,

[0031]Dissolve 136.6g (1.0 equivalent) of tert-butoxyyl chloride in 445mL of acetonitrile, then slowly add the acetonitrile solution of tert-butoxyyl chloride dropwise to the DODA acetonitrile solution at a temperature of 0-5°C, and the dropping time is controlled at 1 -2 hours, after the dropwise addition, stir for 30min, filter, filter the cake with 70mL of acetonitrile: methyl tert-butyl ether = 5:3 mixed solvent rinse, the filter cake after the rinse is dissolved in 1L of water and then oxidized with hydrogen Adjust the pH of the sodium solution to 10, then extract twice with methyl tert-butyl ether, 750 mL each time, combine the organic phases, wash with 250 mL of water, concentrate, and dry to obtain 131.6 g of Boc-1-amino-3,6-bis Oxa-1,8-octanediamine, the purity...

Embodiment 3

[0033] A kind of synthesis technique of Boc-1-amino-3,6-dioxa-1,8-octanediamine, it comprises the steps:

[0034] Add 148.2g DODA and 740mL toluene into a 2L reaction flask, stir and cool down to 0-5°C. Dissolve 150.3g (1.1 equivalent) of tert-butoxyyl chloride in 445mL of toluene, then slowly add the toluene solution of tert-butoxyyl chloride dropwise to the toluene solution of DODA at a temperature of 0-5°C, and the dropping time is controlled at 1 -2 hours, after the dropwise addition, stir for 30 minutes, filter, rinse the filter cake with 70mL of toluene, dissolve the rinsed filter cake with 1L of water, adjust the pH to 10 with sodium hydroxide solution, and then use methyl tert-butyl Extracted twice with ether, 750mL each time, combined the organic phases, washed with 250mL of water, concentrated, and dried to obtain 74.5g of Boc-1-amino-3,6-dioxa-1,8-octanediamine with a purity of 95.3% , yield 30%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of preparation of Boc-1-amino-3,6-dioxa-1,8-octanediamine, in particular to a Boc-1-amino-3,6-dioxa-1,8- Synthetic process of octane diamine. The synthesis process comprises the following steps: taking 3,6-dioxa-1,8-octanediamine and tert-butoxyacyl chloride as raw materials for a one-step substitution reaction, wherein the solvent used in the reaction is selected from acetonitrile, toluene, A mixed solvent of any two of diethyl ether, cyclohexane, n-ethane and chloroform. The synthesis process reaction route of Boc-1-amino-3,6-dioxa-1,8-octanediamine provided by the present invention is simple and the reaction time is short; high yield and high yield can be obtained without complicated purification and separation process. The pure target product is easy to operate and suitable for industrial scale-up production.

Description

technical field [0001] The invention belongs to the technical field of preparation of Boc-1-amino-3,6-dioxa-1,8-octanediamine, in particular to a Boc-1-amino-3,6-dioxa-1,8- Synthetic process of octane diamine. Background technique [0002] Boc-1-amino-3,6-dioxa-1,8-octanediamine is widely used in the pharmaceutical (chemical) industry due to its structural characteristics and functional group characteristics. For example, patent WO2018129557 uses Boc-1-amino-3,6-dioxa-1,8-octanediamine to synthesize a series of tetrahydroisoquinoline derivatives, which can inhibit NHE-mediated sodium ion and hydrogen Reverse transport of ions, which has a positive role in the treatment of disorders associated with fluid retention or salt overload, may be useful in the treatment of gastrointestinal disorders, including the treatment or relief of pain associated with gastrointestinal disorders. Patent WO2006133144 uses Boc-1-amino-3,6-dioxa-1,8-octanediamine to synthesize a peptide compound ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C269/04C07C271/16
Inventor 陈剑戈李斌峰张喜通
Owner 暨明医药科技(苏州)有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com