Method for synthesizing 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl-sulfonyl ethylamine

A technology of methanesulfonylethylamine and methyl methoxybenzoate, which is applied in the field of organic synthesis technology, can solve the problems of high price of benzoate, multiple temperature change steps, difficult control, etc., and achieve stable and low-cost raw materials , low cost, route safety and environmental protection

Inactive Publication Date: 2018-11-06
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The 3-ethoxy-4-methoxy-benzoic acid ester used in this route is expensive, the cost is too high, and the reaction involves more temperature change steps, which is not easy to control

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Preparation of 3-hydroxyl-4-methoxybenzoic acid methyl ester

[0038] Add 15g of 3-hydroxy-4-methoxybenzoic acid, 165ml of methanol, and 540uL of concentrated sulfuric acid to a dry 100mL three-necked flask in sequence, raise the temperature to 55°C, and react overnight under magnetic stirring. Thin-layer chromatography was used to determine the reaction progress, and the developing solvent was ethyl acetate:dichloromethane=1:1. After the completion of the reaction, collect the product, and transfer the product to a round bottom flask for distillation under reduced pressure to remove methanol, extract the residue with 20 mL of ethyl acetate, and add 10 mL of saturated sodium bicarbonate solution for neutralization, take the organic phase, and depressurize Ethyl acetate was distilled off to obtain 11.86 g of solid product methyl 3-hydroxy-4-methoxybenzoate, yield 67.7%.

[0039] (2) Preparation of 3-ethoxyl-4-methoxybenzoic acid methyl ester

[0040] Add 10.36g of ...

Embodiment 2

[0046] (1) Preparation of 3-hydroxyl-4-methoxybenzoic acid methyl ester

[0047] Add 10g of 3-hydroxy-4-methoxybenzoic acid, 110ml of methanol, and 360uL of concentrated sulfuric acid to a dry 100mL three-necked flask in sequence, raise the temperature to 65°C, and react overnight under magnetic stirring. Thin-layer chromatography was used to determine the reaction progress, and the developing solvent was ethyl acetate:dichloromethane=1:1. After the completion of the reaction, collect the product, and transfer the product to a round bottom flask for distillation under reduced pressure to remove methanol, extract the residue with 25 mL of ethyl acetate, and add 15 mL of saturated sodium bicarbonate solution for neutralization, take the organic phase, and depressurize Ethyl acetate was distilled off to obtain 9.06 g of solid product methyl 3-hydroxy-4-methoxybenzoate with a yield of 83.6%.

[0048] (2) Preparation of 3-ethoxyl-4-methoxybenzoic acid methyl ester

[0049] Add 10...

Embodiment 3

[0055] (1) Preparation of 3-hydroxyl-4-methoxybenzoic acid methyl ester

[0056] Add 5g of 3-hydroxy-4-methoxybenzoic acid, 55ml of methanol, and 180uL of concentrated sulfuric acid to a dry 100mL three-necked flask in sequence, raise the temperature to 70°C, and react overnight under magnetic stirring. Thin-layer chromatography was used to determine the reaction progress, and the developing solvent was ethyl acetate:dichloromethane=1:1. After the completion of the reaction, collect the product, and transfer the product to a round-bottomed flask for distillation under reduced pressure to remove methanol, extract the residue with 15 mL of ethyl acetate, and add 8 mL of saturated sodium bicarbonate solution for neutralization, take the organic phase, and depressurize Ethyl acetate was distilled off to obtain 4.67 g of a solid product, methyl 3-hydroxy-4-methoxybenzoate, with a yield of 80.1%.

[0057] (2) Preparation of 3-ethoxyl-4-methoxybenzoic acid methyl ester

[0058] Add...

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PUM

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Abstract

The invention discloses a method for synthesizing 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl-sulfonyl ethylamine and belongs to the technical field of organic synthesis processes. The method comprises the following steps: taking 3-hydroxy-4-methoxybenzoic acid as a raw material, carrying out an esterification reaction to obtain 3-hydroxy-4-methoxybenzoate, reacting with bromoethane to obtain 3-ethyoxyl-4-methoxybenzoate, then reacting with dimethyl sulfone to obtain 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl sulfonyl ethyl ketone, and finally carrying out a reductive amination reaction with ammoniumformate, thereby obtaining the 1-(3-ethyoxyl-4-methoxy)phenyl-2-methyl-sulfonyl ethylamine.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis technology, and relates to a method for preparing apremilast intermediate 1-(3-ethoxy-4-methoxy) by reacting 3-hydroxy-4-methoxybenzoic acid using a batch device The method of phenyl-2-methanesulfonylethylamine. Background technique [0002] Psoriatic arthritis is an inflammatory arthritic condition associated with psoriasis. In psoriasis and psoriatic arthritis, various pro-inflammatory and anti-inflammatory mediators are dysregulated in immune system-related cells such as dendritic cells, monocytes, and chondrocytes. Clinically, the abnormality can be manifested as redness and swelling of the skin, joint swelling and pain, and nail damage, peripheral arthritis, spondyloarthritis, tendon enthesitis, and dactylitis, and is often accompanied by recurrent, mild non-destructive single joints, or Destructive polyarthritis may occur, and osteolysis and joint ankylosis may occur. If not trea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/28
CPCC07C315/04C07C67/08C07C67/31C07C317/28C07C317/24C07C69/734
Inventor 丁晓丹张跃薛鹏博严生虎刘建武沈介发辜顺林马晓明陈代祥刘浩沈禹凡
Owner CHANGZHOU UNIV
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