224448-58-2

Basic information

• Product Name: (5S,6R,7R)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-{2-[(2S)-2-carboxypropyl]-4-methoxyphenyl}-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid
• Synonyms: 5H-Cyclopenta(b)pyridine-6-carboxylic acid, 5-(1,3-benzodioxol-5-yl)-2-butyl-7-(2-((2S)-2-carboxypropyl)-4-methoxyphenyl)-6,7-dihydro-, (5S,6R,7R)-; 5H-cyclopenta[b]pyridine-6-carboxylic acid, 5-(1,3-benzodioxol-5-yl)-2-butyl-7-[2-[(2S)-2-carboxypropyl]-4-methoxyphenyl]-6,7-dihydro-, (5S,6R,7R)-
• CAS NO: 224448-58-2
• Molecular Formula: C₃₁H₃₃NO₇
• Molecular Weight: 531.5962
• Mol File: 224448-58-2.mol

Chemical Properties

• Boiling Point: 705.9°C at 760 mmHg
• Flash Point: 380.7°C
• Density: 1.283g/cm³
• Vapor Pressure: 6.46E-21mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: (5S,6R,7R)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-{2-[(2S)-2-carboxypropyl]-4-methoxyphenyl}-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,6R,7R)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-{2-[(2S)-2-carboxypropyl]-4-methoxyphenyl}-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid(224448-58-2)
• EPA Substance Registry System: (5S,6R,7R)-5-(1,3-benzodioxol-5-yl)-2-butyl-7-{2-[(2S)-2-carboxypropyl]-4-methoxyphenyl}-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid(224448-58-2)

Safety Data

• Hazardous Substances Data: 224448-58-2(Hazardous Substances Data)

Upstream product

• 258349-59-6 5-benzo[1,3]dioxol-5-yl-2-butyl-7-{2-[3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-4-methoxy-phenyl}-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester 
• 247042-78-0 (5S,6R,7R)-5-Benzo[1,3]dioxol-5-yl-2-butyl-7-[2-((S)-3-hydroxy-2-methyl-propyl)-4-methoxy-phenyl]-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid 

Relevant articles and documents

Rate and equilibrium constants for the epimerization of the endothelin receptor antagonist J-104,132 in aqueous solution

The degradation of [5S-[5α,6β,7α(R*)]]-2-butyl-5-(1,3-benzodioxol-5-yl)-7 -[(2-carboxypropyl)-4-methoxyphenyl]-6-dihydro-5H-cyclopenta[b]pyridine-6-car boxylic acid (J-104,132) was studied in aqueous solution as a function of temperature and pH. The degra

Asymmetric conjugate addition reaction

This invention relates to a key intermediate in the synthesis of an endothelin antagonist the synthesis of this key intermediate via an asymmetric conjugate addition reaction.

Practical Asymmetric Synthesis of an Endothelin Receptor Antagonist

An efficient, practical, asymmetric synthesis of the endothelin receptor antagonist 1 is reported. The key pyridine-fused cyclopentane ring bearing three consecutive chiral centers was constructed by first an auxiliary induced asymmetric conjugate addition of the bottom aryllithium from 19 to an unsaturated ester 21 in high diastereoselectivity. After a highly diastereoselective addition of the top aryl Grignard reagent to the aldehyde 22, the alcohol product then underwent a stereospecific intramolecular alkylation of the ester enolate by the phosphate of the alcohol, resulting in the desired trans-trans relative stereochemistry on the cyclopentane ring. The two key chiral centers that set the chirality of the molecule were both induced from cis-1-amino-2-indanol-derived chiral auxiliaries, one in the conjugate addition reaction, the other in setting the chiral center of the bottom side chain via chiral alkylation of an enolate. Oxidation of the primary alcohol to the carboxylic acid in the bottom side chain was carried out with the newly developed TEMPO/bleach-catalyzed oxidation by sodium chlorite (NaClO2) or chromium oxide catalyzed oxidation by periodic acid. The overall process has been run successfully to make multikilograms of the drug in high purity.