Check patentability & draft patents in minutes with Patsnap Eureka AI!

Method for preparing 1,3-dibenzyl-5-formyl-4-alkoxycarbonyl-imidazoline-2-one

An alkoxycarbonyl and dibenzyl technology is applied in the field of preparation of 1,3-dibenzyl-5-formyl-4-alkoxycarbonyl-imidazolin-2-one, and can solve the problem that large-scale industrialization cannot be realized Production, reaction conditions are harsh, application restrictions and other problems, to achieve the effect of large-scale industrial production, high yield, low condition requirements

Inactive Publication Date: 2011-10-12
ZHE JIANG MEDICINE CO LTD XINCHANG PHARMA FAB
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But above-mentioned method adopts DMSO / phosgene, DMSO / oxalyl chloride or DMSO / acetic anhydride, although it can obtain the oxidation product of high yield, yet because the acute toxicity of phosgene, oxalyl chloride is expensive and can cause calculus etc. to people Diseases, DMSO / acetic anhydride reaction yield is very low and other shortcomings limit its application, and the reaction generally needs to be reacted under cryogenic conditions of -60~-78°C, the reaction conditions are harsh, and large-scale industrial production cannot be realized

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
  • Method for preparing 1,3-dibenzyl-5-formyl-4-alkoxycarbonyl-imidazoline-2-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 250ml three-neck flask, nitrogen protection, add DMSO8ml, CH 2 Cl 2 20ml, after cooling to -20°C, slowly add BTC6g and CH 2 Cl 2 30ml of the prepared solution, dropwise, stirred for 0.5h, then slowly added dropwise 1,3-dibenzyl-5-hydroxymethyl-4-methoxycarbonyl-imidazolin-2-one (methanol transesterification product) 15g and CH 2 Cl 2 40ml of the prepared solution, dropwise, stirred for 1h, then slowly added dropwise 20ml of triethylamine and CH 2 Cl 2 20ml of the prepared solution was added and stirred at -20°C for 1 hour after dropping. Remove the freezer, and after naturally warming to room temperature, add 75ml of water, adjust the pH to about 5 with 17.5% HCl, separate the layers, and wash the CH with 20ml of saturated aqueous sodium bicarbonate solution. 2 Cl 2 The extraction layer was washed twice with 20 ml of water, washed with 20 ml of saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate, filtered, and dried CH 2 Cl 2 , add ...

Embodiment 2

[0014] 250ml three-neck flask, nitrogen protection, add DMSO10ml, CHCl 3 20ml, after cooling to -15°C, add BTC9g and CHCl dropwise 3 20ml of the prepared solution, dropwise, stirred for 0.5h, and then added dropwise 1,3-dibenzyl-5-hydroxymethyl-4-ethoxycarbonyl-imidazolidin-2-one (ethanol transesterification) 15g and CHCl 3 40ml of the prepared solution, dropwise, stirred for 1h, then added dropwise 25ml of triethylamine and CHCl 3 20ml of the resulting solution was added and stirred for 1h after dropping. After warming up to room temperature, add 75ml of water, adjust the pH to about 4 with 6% HCl, separate the layers, wash the organic layer twice with 30ml of water, and recover CHCl 3 , add 15ml of toluene, stir to precipitate solid, filter and dry under vacuum at 50°C to obtain 13.1g of target oxidation product 1,3-dibenzyl-5-formyl-4-ethoxycarbonyl-imidazolin-2-one, yield 87.8%.

Embodiment 3

[0016] 250ml three-neck flask, nitrogen protection, add DMSO7ml, CH 2 Cl 2 20ml, after cooling to -10°C, slowly add BTC5.1g and CH 2 Cl 2 20ml of the prepared solution, after dropping, stirred for 0.5h, added dropwise 1,3-dibenzyl-5-hydroxymethyl-4-isopropyloxycarbonyl-imidazolidin-2-one (isopropanol transesterification )15g and CH 2 Cl 2 40ml of the prepared solution, after dropping, stirred for 1h, then slowly added 20ml of triethylamine and CH 2 Cl 2 20ml of the resulting solution was added and stirred for 1h after dropping. After warming up to room temperature, add 75ml of water, adjust the pH to 4.5 with 10% HCl, separate the layers, wash the organic layer twice with water, and recover CH 2 Cl 2 , add 12ml of toluene, stir to precipitate a solid, filter and dry under vacuum at 50°C to obtain 12.7g of the target oxidation product 1,3-dibenzyl-5-formyl-4-isopropyloxycarbonyl-imidazolin-2-one, Yield 85.1%.

[0017] The above are only preferred embodiments of the p...

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 discloses a method for preparing 1, 3-dibenzyl-5-formacyl-4-alkoxycarbonyl-imidazoline-2-ketone. An active agent used by the prior method has various shortcomings so that the application thereof is limited and the reaction thereof is performed under a rigorous condition that the temperature is between 60 DEG C below zero and 78 DEG C below zero. The method uses carbonic acid bi(trichloromethyl ester) and dimethyl sulfoxide to oxidize 1, 3-dibenzyl-5-hydroxymethyl-4-alkoxycarbonyl-imidazoline-2-ketone into the 1, 3-dibenzyl-5-formacyl-4-alkoxycarbonyl-imidazoline-2-ketone in the presence of a solvent. Adopting the carbonic acid bi(trichloromethyl ester) as an activator of the dimethyl sulfoxide, the method can successfully oxidize a DL compound 1, 3-dibenzyl-5-hydroxymethyl-4-alkoxycarbonyl-imidazoline-2-ketone into the 1, 3-dibenzyl-5-formacyl-4-alkoxycarbonyl-imidazoline-2-ketone with high yield, wherein the the requirement on conditions is low, and benzyl and imidazolering which can be easily oxidized in a molecular structure are not affected.

Description

technical field [0001] The invention discloses a preparation method of 1,3-dibenzyl-5-formyl-4-alkoxycarbonyl-imidazolin-2-one. Background technique [0002] In the process of biotin synthesis, the by-product 1,3-dibenzyl-5-hydroxymethyl-4-alkoxycarbonyl-imidazolidin-2-one will be produced. If the mixture 1,3-dibenzyl-5-hydroxymethyl-4-alkoxycarbonyl-imidazolidin-2-one is oxidized to 1,3-dibenzyl-5-formyl-4-alkoxy Carbonyl-imidazolin-2-one, the product can be resolved into a chiral intermediate of biotin, or further oxidized to 1,3-dibenzyl-4,5-cis-biscarboxy-2-imidazolinone, And 1,3-dibenzyl-4,5-cis-biscarboxy-2-imidazolidinone is the starting material for the synthesis of biotin, so as to realize the recycling of by-products, which is a key step in green and clean production. Through screening research, we found that commonly used oxidants such as permanganate, chromic acid oxidation, hydrogen peroxide, oxyacids of chlorine and their salts are difficult to oxidize alcoho...

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): C07D233/34
Inventor 陈建辉沈大冬王勇胡建香
Owner ZHE JIANG MEDICINE CO LTD XINCHANG PHARMA FAB
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com