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

Prepn process of 1-chloro-3-(N-substituent)-tert-butyloxy formylamido-3-substituent-2-acetone

A technology of tert-butoxycarboxamido and acetone is applied in the field of preparing 1-chloro-3--tert-butoxycarboxamido-3-substituted-2-acetone, which can solve the industrial pollution of metal cations and increase the burden of treatment of three wastes , the problem of high price of metal chlorides, to achieve the effect of environmental friendliness, low burden on the three wastes treatment, and low prices

Active Publication Date: 2006-10-04
PORTON FINE CHEM
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Japanese Patent 05-117169 discloses a method for preparing 1-chloro-3-(N-substituted)-tert-butoxycarboxamido-3-substituted-2-acetone with metal chlorides as chlorinated reagents. The price of chemical compounds is relatively high, and the metal cations produced by the reaction also increase the burden of the three wastes treatment, the production cost is high, and the metal cations produced by the reaction have industrial pollution

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
  • Prepn process of 1-chloro-3-(N-substituent)-tert-butyloxy formylamido-3-substituent-2-acetone
  • Prepn process of 1-chloro-3-(N-substituent)-tert-butyloxy formylamido-3-substituent-2-acetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In the laboratory, 35mmol of (3S)-1-diazo-3-tert-butoxycarboxamido-3-methyl-2-propanone was dissolved in a mixed solvent composed of 100ml tetrahydrofuran and 200ml ether, and then the above mixed solution was placed Put it into a 500ml three-necked flask, feed dry 35mmol hydrogen chloride gas under the protection of argon at 0°C, and spin the solvent under reduced pressure to obtain 6.4 g of the desired product as a white solid, with a yield of 83%. Structural identification of the target product, which 1 H nuclear magnetic resonance spectrometer 1 H-NMR (600MHZ, CDCl 3 ) data: δ 1.37 (d, 3H), 1.44 (s, 9H), 4.26 (m, 2H), 5.08 (s, 1H). [α] D 20 = -48.3 (c = 1.0, EtOH). The product was shown to be (3S)-1-chloro-3-tert-butoxycarboxamido-3-methyl-2-propanone.

Embodiment 2

[0019] In the laboratory, 48mmol (3S)-1-diazo-3-tert-butoxycarboxamido-3-(2'-methylpropyl)-2-propanone was dissolved in a mixed solvent composed of 100ml tetrahydrofuran and 200ml ether, Then put the above mixed solution into a 500ml three-neck flask, pass through dry 96mmol hydrogen chloride gas at 10°C under the protection of neon gas, and spin the solvent under reduced pressure to obtain 11.8 grams of the target product as a white solid with a yield of 93%. Structural identification of the target product, which 1 H nuclear magnetic resonance spectrometer 1 H-NMR (600MHZ, CDCl 3 ) data: δ0.9(m, 3H), 0.96(d, 1H), 1.10(m, 3H), 1.14(m, 1H), 1.37(m, 1H), 1.44(s, 9H), 1.90(m , 1H), 4.24(m, 2H), 4.40(m, 1H), 5.0(d, 1H). [α] D 20 = -37.1 (c = 1.0, EtOH). The product was shown to be (3S)-1-chloro-3-tert-butoxycarboxamido-3-(2'-methylpropyl)-2-propanone.

Embodiment 3

[0021] Dissolve 76mmol (±)-1-diazo-3-tert-butoxycarboxamido-3-benzyl-2-propanone in a mixed solvent composed of 100ml tetrahydrofuran and 200ml 1,4-dioxane , and then put the above mixed solution into a 500ml three-necked flask, pass through dry 228mmol hydrogen chloride gas at 25°C under the protection of argon, and spin the solvent under reduced pressure to obtain 21.0 grams of white solid, with a yield of 92.5%. Structural identification of the target product, which 1 H nuclear magnetic resonance spectrometer 1 H-NMR (300MHZ, CDCl 3 ) data: δ1.40 (s, 9H), 3.0-3.1 (m, 2H), 3.9-4.2 (dd, 2H), 4.65 (m, 1H), 5.0 (d, 1H), 7.15-7.24 (d, 2H), 7.3 (m, 3H). [α] D 20 =0 (c=1.0, EtOH). The product was shown to be (±)-1-chloro-3-tert-butoxycarboxamido-3-benzyl-2-propanone.

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 present invention is preparation process of 1-chloro-3-(N-substituent)-tert-butyloxy formylamido-3-substituent-2-acetone. The preparation process has 1-diazo-3-(N-substituent)-tert-butyloxy formylamido-3-substituent-2-acetone as main material and HCl gas as chlorinating reagent, and includes dissolving the main material in dry solvent, introducing dry HCl gas into the solution under the protection of inert gas to react at the temperature from -40 deg.c to +40 deg.c and final decompression drying to eliminate solvent, with the molar ratio between the main material and HCl gas being 1 to 1-10. The preparation process realizes the reaction through controlling the amount of added HCl gas and the reaction temperature, and has low production cost and no industrial pollution caused by metal cation.

Description

technical field [0001] The invention relates to a method for preparing 1-chloro-3-(N-substituted)-tert-butyl by using 1-diazo-3-(N-substituted)-tert-butoxycarboxamido-3-substituted-2-acetone as raw material Oxycarboxamido-3-substituted-2-propanone method. Background technique [0002] Using 1-diazo-3-(N-substituted)-tert-butoxycarboxamido-3-substituted-2-propanone as raw material, hydrogen chloride gas as chlorination reagent to prepare 1-chloro-3-(N-substituted)- tert-butoxycarboxamido-3-substituted-2-acetone, because the tert-butoxyformyl group on the nitrogen atom is very easy to decompose under the condition of hydrogen chloride gas, it is generally believed that this group cannot exist stably when hydrogen chloride gas is introduced, Therefore also there is no bibliographical report that carries out above-mentioned reaction successfully with hydrogen chloride gas as chlorination reagent. Japanese Patent 05-117169 discloses a method for preparing 1-chloro-3-(N-substitu...

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): C07C271/18C07C269/06C07D207/16
Inventor 孙健林川华
Owner PORTON FINE CHEM
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