Unlock instant, AI-driven research and patent intelligence for your innovation.

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

A technology of tert-butoxycarboxamido and acetone, which is applied in the field of preparing 1-chloro-3-tert-butoxycarboxamido-3-substituted-2-acetone, can solve the problem of industrial pollution and increase of metal cations The burden of three wastes treatment and the high price of metal chlorides have achieved the effect of small three wastes treatment burden, low production cost and low price

Active Publication Date: 2005-12-14
PORTON FINE CHEM
View PDF1 Cites 0 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 on the treatment of three wastes, and the production cost is high. At the same time, the metal cations produced by the reaction cause 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
  • Prepn process of 1-chloro-3-(N-substituent)-tert-butyloxy formylamido-3-substituent-2-acetone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] In the laboratory, 35mmol of (3S)-1-diazo-3-tert-butoxycarboxamido-3-methyl-2-acetone was dissolved in a mixed solvent composed of 100ml of tetrahydrofuran and 200ml of ether, and then the above mixed solution was placed Put it into a 500ml three-necked flask, feed dry 35mmol hydrogen chloride gas under argon protection 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, its 1 H NMR 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

[0020] In the laboratory, 48mmol (3S)-1-diazo-3-tert-butoxycarboxamido-3-(2'-methylpropyl)-2-acetone was dissolved in a mixed solvent of 100ml tetrahydrofuran and 200ml ether, The above mixed solution was then put into a 500ml there-necked flask, and 96 mmol of dry hydrogen chloride gas was introduced into it at 10° C. and under the protection of neon gas, and the solvent was spin-dried under reduced pressure to obtain 11.8 g of the desired product, which was a white solid with a yield of 93%. Structural identification of the target product, its 1 H NMR 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

[0022] In the laboratory, 76mmol (±)-1-diazo-3-tert-butoxycarboxamido-3-benzyl-2-acetone was dissolved 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, feed dry 228mmol hydrogen chloride gas under argon protection at 25° C., and spin the solvent under reduced pressure to obtain 21.0 g of white solid with a yield of 92.5%. The structure of the target product was identified, and its 1H NMR 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 kind of preparation of 1-chloro-3-(N-substituted)-tert-butyl by using 1-diazo-3-(N-substituted)-tert-butoxycarboxamido-3-substituted-2-acetone as raw material Method for Oxycarboxamido-3-substituted-2-propanone. Background technique [0002] Using 1-diazo-3-(N-substituted)-tert-butoxycarboxamido-3-substituted-2-acetone as raw material and hydrogen chloride gas as chlorination reagent to prepare 1-chloro-3-(N-substituted)- Tert-butoxycarboxamido-3-substituted-2-acetone, because the tert-butoxycarbonyl group on the nitrogen atom is easily decomposed under the condition of hydrogen chloride gas, it is generally believed that this group cannot exist stably when hydrogen chloride gas is introduced, Therefore, there is no literature report that the above-mentioned reaction has been successfully carried out with hydrogen chloride gas as the chlorination reagent. Japanese Patent 05-117169 discloses a method for preparing 1-chloro-3...

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): C07C271/18
Inventor 孙健林川华
Owner PORTON FINE CHEM