87269-88-3

Usage

Uses

Used in Pharmaceutical Industry:
2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER is used as an active ACE inhibitor for the treatment of hypertension and heart failure. Its ability to inhibit the conversion of angiotensin I to angiotensin II helps in reducing blood pressure and improving cardiovascular function.
Used in Drug Development:
In the field of drug development, 2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER serves as a promising candidate for the development of new medications targeting cardiovascular diseases. Its unique molecular structure allows for further research and modification to enhance its therapeutic effects and minimize side effects.
Used in Chemical Research:
2-[N-[(S)-1-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANYL]-(1S,3S,5S)-2-AZABICYCLO[3.3.0]OCTANE-3-CARBOXYLIC ACID, BENZYL ESTER is also utilized in chemical research for studying the properties and behavior of complex organic compounds. Its colorless oil form and unique molecular structure make it an interesting subject for investigations in organic chemistry and related fields.

Upstream product

• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 87269-87-2 (1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeurebenzylester-hydrochlorid 
• 93779-31-8 benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 87269-87-2 benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 
• 538-75-0 dicyclohexyl-carbodiimide 
• 93779-31-8 benzyl (1R^*,3R^*,5R^*)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 84793-24-8 N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride 
• 100-51-6 benzyl alcohol 
• 765857-50-9 (2S)-2,3,3a,4,5,6-hexahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 87269-85-0 (±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 114192-42-6 N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride 
• 852546-84-0 (2S,3aS,6aS)-benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate 4-toluenesulfonate (1:1) 
• 87269-98-5 (1'S,2S)-2-(1'-Methyl-2'-oxo-2'-phenylmethoxy-ethylamino)-4-oxo-4-phenyl-buttersaeure-ethylester 

Downstream Products

• 87333-19-5 Ramipril 
• 1187092-62-1 ramipril tris(hydroxymethyl)aminomethane salt 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF RAMIPRIL

An enantioselective process for the production of (2S,3aS,6aS)-cyclopenta[b]pyrrole-2-carboxylic acid and its conversion into Ramipril is provided.

A METHOD FOR PREPARING RAMIPRIL

Enantio-specific synthesis of optically pure (2S)-acetylamino-3-(2-oxo-cyclopentyl)- propionic acid (I) comprising converting enantiomeric mixture of (1 -4C alkyl)-2- acetylamino-3-(2-oxocyclopentyl) propionoate (II) (+ and -) under the influence of an Alkaline serine endopeptidase is disclosed. The invention further describes use of optically pure (2S)-acetylamino-3-(2-oxocyclopentyl)-propionic acid (I) formed by the process of present invention, in the preparation of Ramipril.

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.

METHOD FOR THE SYNTHESIS OF A RAMIPRIL INTERMEDIATE

The present invention relates to a process for the preparation of octahydrocyclopenta[b]pyrrole-2-carboxylic acid and esters thereof of general formula (1) in the presence of a cobalt and/or nickel comprising catalyst and to the use of compounds of general formula (1) in the synthesis of ramipril.

NOVEL CARBAMOYLGLYCINE DERIVATIVES

The present invention relates to carbamoylglycine derivatives, a process for the preparation of carbamoylglycine derivatives and the use of carbamoylglycine derivatives in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel carbamoylglycine derivatives.

NOVEL CYCLOALKANONE β-SUBSTITUTED ALANINE DERIVATIVES

The present invention relates to cycloalkanone β-substituted alanine derivatives, a process for the preparation of cycloalkanone β-substituted alanine derivatives and the use of cycloalkanone β-substituted alanine derivatives in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel cycloalkanone β-substituted alanine derivatives.

METHOD FOR THE PRODUCTION OF RAMIPRIL

An improved method for preparing ramipril is disclosed, and also an intermediate for use in the method.

A PROCESS FOR PREPARATION OF RAMIPRIL

Disclosed herein is a process for preparation of Ramipril; which comprises; reacting salts of (S,S,S)-azabicyclo[3.3.0]-octane-3-carboxylate with N-[l-(S)-ethoxy carbonyl)-3- phenyl propyl] -L-alanine in presence of dicyclohexylcarbodimide (DCC) and 1- hydroxybenzotriazole (HOBT) in a suitable solvent medium.

NOVEL 5-SUBSTITUTED HYDANTOINS

The present invention relates to 5-substituted hydantoins, a process for the preparation of 5-substituted hydantoins and the use of 5-substituted hydantoins in the preparation of enantiomerically enriched α-amino acids. Furthermore, the present invention relates to the preparation of pharmaceutically active products such as perindopril and ramipril using the novel 5-substituted hydantoins.

Expeditious synthesis of ramipril: An angiotensin converting enzyme (ACE) inhibitor

We document an efficient and cost-effective synthesis of ramipril 1 utilizing (i) an environmentally benign process for the esterification of racemic 2-aza-bicyclo-[3.3.0]-octane-3-carboxylic acid hydrochloride 2 using boric acid as a catalyst and (ii) a robust resolution process for the synthesis of 3a by means of inexpensive and recyclable L-(+)-mandelic acid as key steps. Copyright Taylor & Francis Group, LLC.