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The production process of (R)-2-((S)-2,2-diMethyl-5-oxo-1,3-dioxolan-4-yl)-3-(naphthalen-2-yl)propanoic acid, also known as Compound X, is a complex and multi-step process that involves various chemical reactions and purification steps.
The following is a detailed overview of the production process of Compound X.
Step 1: Preparation of N-Boc-L-alanine
The first step in the production of Compound X involves the preparation of N-Boc-L-alanine, which is a key intermediate for the synthesis of the desired compound.
N-Boc-L-alanine is prepared by a series of chemical reactions that involve the protection and deprotection of the amino group, followed by the coupling of L-alanine with N-Boc-amino acid.
The reaction conditions and reagents used in this process are optimized to ensure high yield and purity of the product.
Step 2: Condensation of N-Boc-L-alanine with 2,2-dimethyl-5-oxo-1,3-dioxolan-4-one
The second step involves the condensation of N-Boc-L-alanine with 2,2-dimethyl-5-oxo-1,3-dioxolan-4-one in the presence of a strong condensing agent, such as dicyclohexylcarbodiimide (DCC).
The reaction is carried out under controlled conditions, such as room temperature and with a polar protic solvent, such as DMF.
The purpose of using a polar solvent is to improve the solubility of the reactants, ensure a uniform reaction, and facilitate the removal of the formed HCl salt.
Step 3: Cyclization of the Intermediate Product
The next step involves the cyclization of the intermediate product, which is a highly reactive carbonyl compound.
Cyclization is achieved by treating the intermediate product with a strong base, such as sodium hydroxide, in the presence of a solvent, such as water.
The purpose of using a base is to neutralize the carboxylic acid and promote the formation of the desired cyclic compound.
Step 4: Protection of the Cyclic Intermediate
The next step is the protection of the newly formed cyclic intermediate.
This involves the installation of a protecting group, such as benzyl bromide, onto the hydroxyl group of the cyclic compound.
This step is necessary to prevent further reactions that could lead to unwanted side products or degradation of the compound.
Step 5: Deprotection of the Benzyl Group
The next step involves the deprotection of the benzyl group, which is achieved by treating the compound with a reagent that selectively cleaves the benzyl group, such as hydrogen bromide in acetic acid.
This step is necessary to liberate the desired product, which is further purified and characterized.
Step 6: Purification of the Product
The final step involves the purification of the product, which is achieved by using several purification techniques, such as column chromatography, recrystallization, and high-performance liquid chromatography (HPLC).
These techniques are used to remove any remaining impurities and ensure the highest possible purity of the final product.
In conclusion, the production of (R)-2-((S)-2,2-diMethyl-5-oxo-1,3-dioxolan-4-yl)-3-(naphthalen-2-yl)propanoic acid, or Compound X, involves several chemical reactions and purification steps.
The process requires careful optimization of reaction conditions, selection of appropriate reagents, and purification techniques to ensure the highest possible yield and purity of the final product.
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