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The Instruction of 4-[[[2-(Diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester is a complex organic compound used in various chemical reactions to synthesize other chemicals and materials.
This compound has several unique properties that make it an ideal substrate for various chemical transformations.
In this article, we will discuss the instruction of 4-[[[2-(Diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester, its synthesis, and its applications in the chemical industry.
Introduction:
4-[[[2-(Diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester is a synthetic organic compound that is used as a building block in organic synthesis.
It is structurally derived from pyrrole, a basic aromatic amino acid with a simple molecular formula.
The compound is characterized by its unique chemical properties, including its ability to undergo various chemical reactions, such as electrophilic substitution, electrophilic addition, and asymmetric synthesis.
Synthesis:
The synthesis of 4-[[[2-(Diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester involves several steps, including the preparation of the appropriate starting materials, the reaction conditions, and the purification of the final product.
Here is a general outline of the synthesis procedure:
- Preparation of the starting materials:
The synthesis of 4-[[[2-(Diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester requires several starting materials, including dimethyl 3-oxopropionate, 2-pyrrole carboxaldehyde, diethylamine, acetic acid, and tert-butyl bromide.
- Coupling reaction:
The coupling reaction is carried out by mixing the dimethyl 3-oxopropionate and 2-pyrrole carboxaldehyde in the presence of a polar protic solvent, such as water or DMF.
The reaction is carried out at an elevated temperature, typically between 80-100°C, with the addition of a catalyst, such as NaOH or KOH.
The reaction mixture is stirred for several hours to allow the reaction to proceed to completion.
- Deprotection:
After the reaction is complete, the tert-butyl ester group is protected with a acid-sensitive protecting group, such as TBS (tert-butyldimethylsilyl) or TBDMS (tert-butyldimethylsilyl).
This protecting group is added to the alcohol function of the intermediate to prevent any unwanted reactions that could occur during the subsequent steps.
- Dehydration:
The dehydration step is carried out by treating the intermediate with a strong acid, such as HCl or P2O5.
The reaction mixture is stirred at room temperature for several hours to allow the reaction to proceed to completion.
- Coupling reaction with amino acid:
The next step involves the coupling of the 4-[[[2-(Diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester with a suitable amino acid, such as L-alanine or L-glutamic acid.
This reaction is carried out in the presence of a condensing agent, such as dicyclohexylcarbodiimide (DCC) or