1356932-13-2

Usage

Uses

Used in Pharmaceutical Industry:
Enalapril EP IMpurity A (SSR) is used as an impurity in the production of Enalapril maleate for the treatment of high blood pressure and heart failure. It is essential to control the presence of this impurity to ensure the safety and efficacy of the final drug product.

Upstream product

• 75847-73-3 enalapril 
• 110-16-7 maleic acid 
• 147-85-3 L-proline 
• 406213-94-3 C₁₈H₂₆N₂O₄ 
• 2812-46-6 proline tert-butyl ester 
• 80828-26-8 N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine hydrochloride 
• 288-32-4 1H-imidazole 
• 7732-18-5 water 
• 877932-98-4 N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine 
• 82009-36-7 N-[N-(1-(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl]-L-proline 
• 120924-94-9 N-<(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl>-L-alanyl-L-proline Benzylester 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 108428-39-3 N--L-alanyl>-L-proline tert butyl ester 
• 80828-38-2 N-<(S)-1-(ethoxycarbonyl)-3-phenylpropyl>-L-alanine tert-butylester 

Downstream Products

• 196083-21-3 enalaprilate 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE

A process for the production of amides of N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine is described. The process can be used for the production of key intermediates and finally the ACE inhibitors such as Ramipril, Enalapril, Quinapril, Trandolapril, Delapril and Moexipril starting from N-[1-(S)-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine by the reaction with the appropriate amines.

A PROCESS FOR THE PREPARATION OF COMPOUNDS HAVING AN ACE INHIBITORY ACTION

The present invention relates to the process for the preparation of compounds of formula (I) having an ACE inhibitory action wherein carboxy group of stereospecific amino acid is activated with an uronium salt in in the presence of an aprotic solvent and an activated amino acid is further transformed with appropriate amine into ACE inhibitor or its precursor.

Soluble alpha-amino acid salts in acetonitrile: practical technology for the production of some dipeptides.

Alpha-amino acids are soluble in acetonitrile when treated with phosphazene bases. As a result, the protection/deprotection events that are usually required for peptide coupling reactions can be minimized. This is illustrated in the synthesis of the important angiotensin-converting enzyme (ACE) inhibitor enalapril. [reaction: see text]

Process for preparing pharmacologically acceptable salt of N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl amino acids

There is provided a process for preparing a pharmacologically acceptable salt of N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-amino acid which comprises condensing an amino acid and N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanine.N-carboxyanhydride under basic condition, carrying out decarboxylation under between neutral and acidic condition to obtain N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-amino acid, and forming a pharmacologically acceptable salt thereof, wherein the production of a by-product (3): is suppressed by carrying out in an aqueous liquid a series of operations till formation of the pharmacologically acceptable salt or till isolation of the pharmacologically acceptable salt. The present invention enables to prepare the pharmacologically acceptable salt of N-(1(S)-ethoxycarbonyl-3-phenylpropyl)-L-alanyl-amino acid having high quality, in a commercial scale with high yield and economical efficiency.

Process for preparing carboxyalkyl dipeptides

Pharmaceutically active carboxyalkyl dipeptides such as enalapril, lisinopril and the like, are prepared from a starting amino acid such as L-alanine, by protecting the acid function of the amino acid with an alkyl silyl protecting group, while it is reacted with an α-halo ester, at its amino function. Subsequently, the silyl protectant is removed, and the acid group is reacted with the amino function of an appropriate amino acid such as L-proline, to form the dipeptide product.

Process for preparing N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-L-proline

A process for preparing N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanyl-L-proline, which comprises reacting N-carboxyanhydride of N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine with L-proline in the presence of a base. According to the process, enalapril can be prepared economically, easily and effectively.

Process for preparing carboxyalkyl dipeptides

A process is disclosed for preparing carboxyalkyl dipeptides of the formula: STR1