87269-87-2

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride is used as a key intermediate in the preparation of ramipril, an angiotensin-converting enzyme (ACE) inhibitor. It plays a crucial role in the development of this medication, which is used to treat hypertension, heart failure, and other cardiovascular conditions.
Additionally, (1S,3S,5S)-2-Azabicyclo[3,3,0]octane-3-carborylic acid benzyl ester hydrochloride serves as a starting material for the synthesis of octahydrocyclopenta[b]pyrrole-2-carbonitrile derivatives. These compounds are potent DPP4 inhibitors, which are used in the treatment of type 2 diabetes by increasing the levels of insulin and decreasing blood sugar levels.

InChI:InChI=1/C15H19NO2.ClH/c17-15(18-10-11-5-2-1-3-6-11)14-9-12-7-4-8-13(12)16-14;/h1-3,5-6,12-14,16H,4,7-10H2;1H/t12-,13-,14?;/m0./s1

Upstream product

• 87269-87-2 (1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeurebenzylester-hydrochlorid 
• 93779-32-9 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 
• 93779-31-8 benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 100-51-6 benzyl alcohol 
• 135214-79-8 S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt 
• 765857-50-9 C₈H₁₁NO₂ 
• 1296306-77-8 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid 
• 94569-19-4 2-aza-bicyclo[3.3.0]octane-3-carboxylic acid benzyl ester hydrochloride 
• 1296242-98-2 C₁₅H₁₇NO₂ 
• 59983-35-6 Cyclopentylidene-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 109428-53-7 (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 120-92-3 cyclopentanone 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 87269-85-0 (±)-methyl 2-(acetylamino)-3-(2-oxocyclopentyl)-propionate 

Downstream Products

• 126110-93-8 (2S,3aS,6aS)-1-((S)-6-Benzyloxycarbonylamino-2-hydroxy-hexanoyl)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 
• 93779-31-8 benzyl (1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylate 
• 87269-88-3 2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester 
• 124002-38-6 (2S,3aS,6aS)-2-benzyl 1-tert-butyl hexahydrocyclopenta[b]pyrrole-1,2(2H)-dicarboxylate 
• 2387-23-7 1,3-Dicyclohexylurea 
• 1044591-63-0 C₄₃H₆₄N₄O₂ 
• 1005495-74-8 C₄₃H₆₄N₄O₄ 
• 124002-32-0 (2S,3aS,6aS)-1-[(tert-butoxy)carbonyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 87333-19-5 Ramipril 
• 87269-87-2 benzyl (2S,3AS,6AS)-octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride 
• 109428-53-7 (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid 
• 135214-79-8 S,S,S-2-azabicyclo[3,3,0]-octane-3-carboxylic acid benzyl ester L-mandelic acid salt 
• 87269-86-1 (S,S,S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid hydrochloride 
• 93779-32-9 (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid; compound with (2S,3aS,6aS)-octahydro-cyclopenta[b]pyrrole-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Shape Similarity by Fractal Dimensionality: An Application in the de novo Design of (?)-Englerin A Mimetics

Molecular shape and pharmacological function are interconnected. To capture shape, the fractal dimensionality concept was employed, providing a natural similarity measure for the virtual screening of de novo generated small molecules mimicking the structurally complex natural product (?)-englerin A. Two of the top-ranking designs were synthesized and tested for their ability to modulate transient receptor potential (TRP) cation channels which are cellular targets of (?)-englerin A. Intracellular calcium assays and electrophysiological whole-cell measurements of TRPC4 and TRPM8 channels revealed potent inhibitory effects of one of the computer-generated compounds. Four derivatives of this identified hit compound had comparable effects on TRPC4 and TRPM8. The results of this study corroborate the use of fractal dimensionality as an innovative shape-based molecular representation for molecular scaffold-hopping.

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.

Asymmetric synthesis of (S,S,S)-2-Aza-bicyclo-[3.3.0]-octane-3-carboxylic acid benzyl ester: Formal synthesis of ramipril

An asymmetric synthesis of (S,S,S)-2-aza-bicyclo-[3.3.0]-octane-3- carboxylic acid benzyl ester 2 as an intermediate of angiotensin converting enzyme (ACE) inhibitor, ramipril 1, is described.

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.

METHOD FOR THE PRODUCTION OF RAMIPRIL

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

PREPARATION OF RAMIPRIL AND STABLE PHARMACEUTICAL COMPOSITIONS

A process for preparing ramipril, and stable pharmaceutical compositions containing ramipril.

SYNTHESIS OF UNNATURAL AMINO ACIDS: (S,S,S)-2-AZABICYCLOOCTANE-3-CARBOXYLIC ACID

(S,S,S)-2-Azabicyclooctane-3-carboxylic acid 1, a structural element of the very potent ACE inhibitor HOE 498, is readily available via a diastereo selective synthesis starting from serine or cystine.

Synthesis of a highly active angiotensin converting enzyme inhibitor: 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyc lo[3.3.0]octane-3-carboxylic acid (Hoe 498)

The convergent, diastereoselective synthesis of 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyc lo[3.3.0]octane-3-carboxylic acid (Hoe 498), a new ACE-inhibitor with improved bioavailability and pharmacokinetics, is described.