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Method of de-alkyl amine

A technology for removing tertiary alkylamines and tertiary alkylamides, which is applied in organic chemical methods, chemical instruments and methods, amide preparation, etc., can solve problems such as low yield and strong reaction conditions, and avoid hydrolysis conditions and reaction processes Choose a reasonable effect

Active Publication Date: 2009-10-07
上海药明康德新药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The purpose of the present invention is to develop a mild method for removing tertiary alkylamines, through hydrolysis of tertiary alkylamides into carboxylic acids, mainly to solve the technical problems of too strong reaction conditions and low yield in known methods

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0020]

[0021] Add 50ml of water to a 250ml round bottom flask, slowly add 50ml of trifluoroacetic acid under ice cooling, keep the internal temperature below 25°C, then add (5g, 0.024mol) of N-tert-butyl in batches at the same temperature p-methoxybenzamide. After feeding, adjust the reaction temperature to 99°C until the reaction solution is clear, and then heat and reflux at a constant temperature for 24 hours. Sampling is detected by TLC plate, and the hydrolysis reaction is completed. The reaction solution was evaporated to dryness by a rotary evaporator under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate, washed once with 30 mL of saturated brine, twice with 50 mL of deionized water, dried over anhydrous sodium sulfate, then filtered and concentrated by spinning under reduced pressure. The product was purified by column chromatography to obtain 2.55 g of p-methoxybenzoic acid (FW=152.15, 0.0168 mol), and the conversion rate was 70%. 1 H ...

Embodiment 2

[0023]

[0024] Add 66.6ml of water into a 250ml round-bottomed flask, slowly add 33.3ml of trifluoroacetic acid under cooling in an ice bath, keep the internal temperature below 25°C, then add (5g, 0.024mol) of N- tert-butyl-p-methoxybenzamide. After feeding, adjust the reaction temperature to 99°C until the reaction solution is clear, and then heat and reflux at a constant temperature for 24 hours. Sampling is detected by TLC plate, and the hydrolysis reaction is complete. The reaction solution was evaporated to dryness by a rotary evaporator under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate, washed once with 30 mL of saturated brine, twice with 50 mL of deionized water, dried over anhydrous sodium sulfate, then filtered and concentrated by spinning under reduced pressure. The product was purified by column chromatography to obtain 2.88 g of the product p-methoxybenzoic acid (FW=152.15, 0.0191 mol), and the conversion rate was 79%.

[0025]...

Embodiment 3

[0027]

[0028] Add 75ml of water to a 250ml round bottom flask, slowly add 25ml of trifluoroacetic acid under ice-bath cooling, keep the internal temperature below 25°C, then add (5g, 0.024mol) of N-tert-butyl in batches at the same temperature p-methoxybenzamide. After the feeding is completed, adjust the reaction temperature to 98°C~99°C until the reaction solution is clear, and heat and reflux at a constant temperature for 36 hours. Sampling is detected by TLC plate, and the hydrolysis reaction is completed. The reaction solution was evaporated to dryness by a rotary evaporator under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate, washed once with 30 mL of saturated brine, twice with 50 mL of deionized water, dried over anhydrous sodium sulfate, then filtered and concentrated by spinning under reduced pressure. The product was purified by column chromatography to obtain 2.47 g of the product p-methoxybenzoic acid (FW=152.15, 0.0162 mol), with...

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Abstract

The invention relates to a method of de-tert-alkyl amine, which mainly solves the technical problems of over strong reacting conditions and low yield of the prior method. The method of de-tert-alkyl amine is characterized in that tertiary tert-alkyl acid amide is reacted in the mixed solution of trifluoroacetic acid and water and is hydrolyzed into corresponding carboxylic acids, the volume ratio of the trifluoroacetic acid and water is 1-100: 0-5, and the reacting formula is as above. In the formula, R and R' are the alkyl group or the aromatic group of C1 to C20, and the reaction temperature is from the room temperature to the solvent reflux temperature. The invention hydrolyzes the tertiary tert-alkyl amine into corresponding carboxylic acids under a mild condition.

Description

Technical field: [0001] The invention relates to a method for removing tertiary alkylamines, through mild hydrolysis of tertiary alkylamines into corresponding carboxylic acids. Background technique: [0002] Tertiary alkyl amines, especially tertiary amide, are useful intermediates in organic synthesis. In many syntheses, the carboxylic acid is first converted into tertiary amide, and then a series of molecules are carried out through tertiary amide chemistry or reactivity. Modification, and finally hydrolysis of tertiarylamide back to carboxylic acid. For the hydrolysis of tertiary alkyl amides, because of the large steric hindrance of tertiary alkyl, the reaction conditions are mostly severe, and the current literature reports mainly include the following conditions. [0003] A strong acid hydrolysis: [0004] 1. Aqueous sulfuric acid solution (10% to 70%). [0005] 2.6N mixed solution of hydrochloric acid and glacial acetic acid (hydrochloric acid: glacial acetic acid...

Claims

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Application Information

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IPC IPC(8): C07B41/08C07C51/06C07C63/06C07C65/21C07D333/40
Inventor 张科许金峰高兴柱彭宪施一峰马汝建陈曙辉
Owner 上海药明康德新药开发有限公司
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