82717-91-7

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, octahydro-, phenylMethyl ester, 4-Methylbenzenesulfonate (1:1)
• Synonyms: 1H-Indole-2-carboxylic acid, octahydro-, phenylMethyl ester, 4-Methylbenzenesulfonate (1:1);Benzyl octahydro-1H-indole-2-carboxylate 4-methylbenzenesulfonate
• CAS NO: 82717-91-7
• Molecular Formula: C23H29NO5S
• Molecular Weight: 431.54506
• Mol File: 82717-91-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, octahydro-, phenylMethyl ester, 4-Methylbenzenesulfonate (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, octahydro-, phenylMethyl ester, 4-Methylbenzenesulfonate (1:1)(82717-91-7)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, octahydro-, phenylMethyl ester, 4-Methylbenzenesulfonate (1:1)(82717-91-7)

Safety Data

• Hazardous Substances Data: 82717-91-7(Hazardous Substances Data)

Usage

Molecular weight

357.46 g/mol

Appearance

White to off-white powder

Uses

Commonly used in the pharmaceutical and chemical industries for various applications

Toxicity

Potential to be toxic if ingested or inhaled, should be handled with care in a controlled laboratory environment.

Upstream product

• 100-51-6 benzyl alcohol 
• 881637-65-6 (3aR,7aS)-perhydroindole-2-carboxylic acid 
• 104-15-4 toluene-4-sulfonic acid 
• 16851-56-2 indolin-2-yl carboxylic acid 
• 80828-13-3 (+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid 
• 79815-20-6 (S)-indoline-2-carboxylic acid 
• 80875-98-5 (2S,3aS,7aS)-perhydroindole-2-carboxylic acid 

Relevant articles and documents

Process for the preparation of intermediates of perindopril

A process for the preparation of (2S, 3aS, 7aS)perhydroindole-2-carboxylic acid is provided comprising (a) esterifying a cis-perhydroindole-2-carboxylic acid with a first alcohol of the formula ROH and a suitable free acid to provide the acid salt (AS) of Formula V: (b) reacting the acid salt of Formula V with a first base to provide a compound of Formula VI: (c) treating the product of step (b) with an L-tartaric containing acid in a second alcohol of the formula ROH to precipitate a compound of Formula VII: (d) reacting the compound of Formula VII with a second base to provide a compound of Formula II (e) hydrolyzing the compound of Formula II to provide the (2S, 3aS, 7aS)perhydroindole-2-carboxylic acid.

Efficient access to N-protected derivatives of (R,R,R)- and (S,S,S)-octahydroindole-2-carboxylic acid by HPLC resolution

The preparation of the proline analogue (2S,3aS,7aS)-octahydroindole-2-carboxylic acid (Oic) and its enantiomer, (2R,3aR,7aR)-Oic, is described. A racemic precursor has been synthesized in good yield and subjected to HPLC resolution on a chiral column. The high efficiency of both the synthetic and chromatographic procedures has allowed the isolation of multigram quantities of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis.

Novel method for synthesissing (2s,3as,7as)-perhydroindole-2-carboxylic acid and the esters thereof and the use thereof for perindopril synthesis

Process for the synthesis of compounds of formula (I): wherein R represents hydrogen or a protecting group. Application in the synthesis of perindopril and pharmaceutically acceptable salts thereof.

Process for the preparation of intermediates of trandolapril and use thereof for the preparation of trandolapril

A process for the preparation of an intermediate of trandolapril, (2S,3aR,7aS)-perhydroindole-2-carboxylic acid of Formula II is provided. Also provided are processes for preparing trandolapril.

Configuration and preferential solid-state conformations of perindoprilat (S-9780). Comparison with the crystal structures of other ACE inhibitors and conclusions related to structure-activity relationships

The conformation of perindoprilat, an antihypertensive drug, is studied in the solid state by X-ray analysis. The resolution of its structure reveals important analogies between its observed conformation and that of several ACE inhibitors of the same family. This comparison points out a constant relative orientation of the functional groups, regardless of the molecular environment. This angular constancy appears to us as not being accidental and is a good argument for the spatial design of the ACE binding site. Although ACE is a carboxydipeptidase, the binding site may not contain two but one unique hydrophobic pocket receiving the C-terminal end of the inhibitors.