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

Synthesis method of diamido ortho-ester monomer

A technology of diamino ortho ester and synthesis method, which is applied in the field of synthesis of diamino ortho ester monomer, can solve problems such as long reaction time, uncontrollable molecular weight, sensitivity to light and moisture, and achieve economical and high yield , raw materials are easy to obtain, and the synthesis process is simple

Inactive Publication Date: 2010-10-27
JIANGNAN UNIV
View PDF9 Cites 14 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, these two synthetic methods all have relatively large limitations: the transesterification method requires high temperature, high pressure, long reaction time and uncontrollable molecular weight and other shortcomings, and this method has no longer been developed; although the addition polymerization method has achieved relatively Great success, but requires a bis(ketene acetal) monomer (DETOSU) (Chinese patent 1726177A; US patent 4513143; US patent 4532335), which is very sensitive to light and moisture, preparation, storage And use requires harsh conditions

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
  • Synthesis method of diamido ortho-ester monomer
  • Synthesis method of diamido ortho-ester monomer
  • Synthesis method of diamido ortho-ester monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthetic method of 4-aminomethyl-2-aminopentyloxy-[1,3]dioxane monomer is realized through the following steps:

[0029] 1) Preparation of 2,2,2-trifluoro-N-(2,3-dihydroxypropanol)

[0030] Under a nitrogen atmosphere, add 18.80 g (0.21 mol) of 3-amino-1,2-propanediol and 120 ml of acetonitrile to a 250 ml three-necked flask, and slowly add 34.30 g (0.24 mol) of ethyl trifluoroacetate dropwise at 0°C, at room temperature After reacting for 4 hours and evaporating the volatile reagents under reduced pressure, the crude product was dissolved in ethyl acetate, washed with aqueous potassium bisulfate solution (0.5M) and saturated brine, dried over magnesium sulfate, evaporated under reduced pressure to remove the solvent, and dried in vacuo to obtain colorless The oily pure product was 34.90g, and the yield was 91%. 1 H NMR (300MHz, CD 3 OD): δ (ppm) 3.27-3.29 (m, 2H, NH-CH 2 ), 3.47-3.49 (m, 2H, CH 2 -OH), 3.70-3.78 (m, 1H, CH-OH), 7.60 (b, 1H, NH).

[0031] 2) P...

Embodiment 2

[0038] The synthetic method of 4-aminomethyl-2-aminopentyloxy-2-methyl-[1,3]dioxane monomer is realized through the following steps:

[0039] 1) Preparation of 2,2,2-trifluoro-N-(2,3-dihydroxypropanol)

[0040] Under a nitrogen atmosphere, add 18.80 g (0.21 mol) of 3-amino-1,2-propanediol and 120 ml of acetonitrile to a 250 ml three-necked flask, and slowly add 34.30 g (0.24 mol) of ethyl trifluoroacetate dropwise at 0°C, at room temperature After reacting for 4 hours and evaporating the volatile reagents under reduced pressure, the crude product was dissolved in ethyl acetate, washed with aqueous potassium bisulfate solution (0.5M) and saturated brine, dried over magnesium sulfate, evaporated under reduced pressure to remove the solvent, and dried in vacuo to obtain colorless The oily pure product was 34.90g, and the yield was 91%. 1 H NMR (300MHz, CD 3 OD): δ (ppm) 3.27-3.29 (m, 2H, NH-CH 2 ), 3.47-3.49 (m, 2H, CH 2 -OH), 3.70-3.78 (m, 1H, CH-OH), 7.60 (b, 1H, NH).

[0...

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 relates to a synthesis method of diamido ortho-ester monomer, which belongs to the technical field of organic chemistry and biomaterials. The diamido ortho-ester monomer is 4-aminomethyl-2-amino pentyloxy-2-R group-[1,3] dioxane as shown in formula I, wherein the R group is hydrogen or methyl, and the diamido ortho-ester monomer is a new generation of ortho-ester monomer in a brand-new structure. The synthesis method of the diamido ortho-ester monomer comprises the following steps that: 3-amino-1,2-propanediol is taken as the raw material, reacts with trimethyl ortho ester under the action of an acid catalyst after reacting with ethyl trifluoroacetate to protect the amino, the obtained product exchanges and reacts with 5-trifluoroacetyl amino pentanol ester under the action of the catalyst to obtain a monomer precursor, and finally the precursor is added into lye to remove a trifluoroacetyl protecting group so as to obtain the diamido ortho-ester monomer. The synthesis method has the advantages of easily available raw materials, simple synthesis process and higher economy and yield and is applicable to large-scale industrial production; and simultaneously, the monomer is extremely stable at normal temperature, and can be used for the research and development of a new generation of poly ortho ester polymer biomaterials.

Description

technical field [0001] The invention relates to a method for synthesizing a diamino orthoester monomer, which belongs to the technical field of organic chemistry and biological materials. Background technique [0002] Polyorthoesters (Polyorthoesters, POE) is an acid-sensitive and biodegradable polymer material. Since it was first synthesized by Jorge Heller and his colleagues in the United States in the 1960s, because of its good surface controllable erosion performance, it has been widely used in drug slowdown. The field of controlled release has developed rapidly. At present, the sustained-release preparations of anti-tumor drugs and anti-narcotic antagonists of this excipient are undergoing phase III clinical trials, and are expected to be approved by the US FDA. [0003] Polyorthoesters have been developed for four generations (Biomacromolecules 2004, 5, 1625-1632; Adv.Drug Deliv.Rev.2002, 54, 1015-1039), and their synthesis methods are divided into polyvalent orthoest...

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
IPC IPC(8): C07D317/34
CPCY02P20/55
Inventor 唐汝培
Owner JIANGNAN UNIV
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