80876-01-3

Basic information

• Product Name: Indolapril
• Synonyms: Indolapril;Sch 31846
• CAS NO: 80876-01-3
• Molecular Formula: C24H34N2O5
• Molecular Weight: 430.542
• Mol File: 80876-01-3.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 626°C at 760 mmHg
• Flash Point: 332.4°C
• Appearance: /
• Density: 1.181g/cm³
• Vapor Pressure: 1.55E-16mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: Indolapril(CAS DataBase Reference)
• NIST Chemistry Reference: Indolapril(80876-01-3)
• EPA Substance Registry System: Indolapril(80876-01-3)

Safety Data

• Hazardous Substances Data: 80876-01-3(Hazardous Substances Data)

Usage

Uses

Antihypertensive.

InChI:InChI=1/C24H34N2O5/c1-3-31-24(30)19(14-13-17-9-5-4-6-10-17)25-16(2)22(27)26-20-12-8-7-11-18(20)15-21(26)23(28)29/h4-6,9-10,16,18-21,25H,3,7-8,11-15H2,1-2H3,(H,28,29)/t16-,18-,19-,20-,21-/m0/s1

Upstream product

• 84793-24-8 N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride 
• 145438-94-4 (2S,3aR,7aS)-octahydroindolecarboxylic acid 
• 114192-42-6 N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride 
• 881637-74-7 (2S,3aR,7aS)-perhydroindole-2-carboxylic acid trimethyl silyl ester 
• 82717-90-6 cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 80828-13-3 rac-trans-octahydroindole-2-carboxylic acid 
• 530-62-1 1,1'-carbonyldiimidazole 
• 124492-03-1 N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester 
• 237421-54-4 tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate 
• 237421-53-3 tert-butyl (2S,4S)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 35418-16-7 L-t-butyl pyroglutamate 

Relevant articles and documents

A Stereoselective Synthesis of the ACE Inhibitor Trandolapril

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l -pyroglutamic acid derivative, a highly diastereoselective Hosomi-Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

PROCESS FOR THE SYNTHESIS OF AN ACE INHIBITOR

A process for the synthesis of trandolapril which comprises condensing N-[I-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride with trans octahydro-1H- indole-2-carboxylic acid in a first organic solvent comprising a water immiscible inert organic solvent and in the presence of a base, and isolating trandolapril from a second organic solvent. N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride may also be condensed with (2S,3aR,7aS) octahydro-1H-indole-2-carboxyIic acid in a first organic solvent and in the presence of a base, and trandolapril isolated. There is also provided a process for the resolution of racemic trans octahydro-1H-indole-2-carboxylc acid.

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.