173399-03-6

Basic information

• Product Name: (2S,4S,5S,7S)-7-(3-(3-Methoxypropoxy)-4-methoxybenzyl)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hydrochloride
• Synonyms: (2S,4S,5S,7S)-7-(3-(3-Methoxypropoxy)-4-methoxybenzyl)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hydrochloride;Aliskiren Hydrochloride;(αS,γS,δS,zS)-δ-AMino-N-(3-aMino-2,2-diMethyl-3-oxopropyl)-γ-hydroxy-4-Methoxy-3-(3-Methoxypropoxy)-α,z-bis(1-Methylethyl)benzeneoctanaMide Hydrochloride;Rasilez Hydrochloride;Tekturna Hydrochloride;(2S,4S,5S,7S)-5-AMino-N-(3-aMino-2,2-diMethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-(4-Methoxy-3-(3-Methoxypropoxy)benzyl)-8-MethylnonanaMide hydrochloride
• CAS NO: 173399-03-6
• Molecular Formula: C₃₀H₅₃N₃O₆*ClH
• Molecular Weight: 588.22
• Product Categories: Amines;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 173399-03-6.mol

Chemical Properties

• Melting Point: 76-78°C
• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform, Methanol
• Stability: Hygroscopic
• CAS DataBase Reference: (2S,4S,5S,7S)-7-(3-(3-Methoxypropoxy)-4-methoxybenzyl)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S,5S,7S)-7-(3-(3-Methoxypropoxy)-4-methoxybenzyl)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hydrochloride(173399-03-6)
• EPA Substance Registry System: (2S,4S,5S,7S)-7-(3-(3-Methoxypropoxy)-4-methoxybenzyl)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide hydrochloride(173399-03-6)

Safety Data

• Hazardous Substances Data: 173399-03-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Upstream product

• 173338-07-3 tert-butyl (3S,5S,6S,8S)-8-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-6-hydroxy-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-2,9-dimethyldecan-5-ylcarbamate 
• 325154-31-2 (2S,4S,5R,7S)-5-Azido-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide 
• 1200341-42-9 (1S,3S,4R,7S,9R)-3,7-diisopropyl-4-(4-methoxy-3-(3-methoxypropoxy)-phenyl)-6-oxo-5-oxa-10-aza-bicyclo[7.1.0]decane-10-sulfonic acid 2,2,2-trichloro-ethyl ester 
• 1200341-46-3 (2R,2'S,3S,4'S,5S)-3-isopropyl-5-(4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-2-(4-methoxy-3-(3-methoxypropoxy)-phenyl)-pyrrolidine-1-sulfonic acid 2,2,2-trichloro-ethyl ester 
• 1219468-79-7 (2R,3S,5S)-2,2,2-trichloroethyl 5-((1S,3S)-3-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-1-hydroxy-4-methylpentyl)-3-isopropyl-2-(4-methoxy-3-(3-methoxypropoxy)phenyl)pyrrolidine-1-sulfonate 
• 916793-76-5 (2R,3S,5S)-tert-butyl 5-((1S,3S)-3-(3-amino-2,2-dimethyl-3-oxopropylcarbamoyl)-1-hydroxy-4-methylpentyl)-3-isopropyl-2-(4-methoxy-3-(3-methoxypropoxy)phenyl)pyrrolidine-1-carboxylate 

Downstream Products

• 173334-58-2 (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate 

Relevant articles and documents

The development of a complementary pathway for the synthesis of aliskiren

The synthesis of aliskiren (1), a recently marketed drug for the treatment of hypertension, is presented. The focus of our synthetic effort is to develop an efficient pathway for the synthesis of (2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy) benzyl)-N,N,8-trimethylnon-4-enamide (2a), which has been used as the advanced intermediate toward aliskiren. After an extensive investigation of three different strategies designed to construct the E-olefin functionality in 2a by employing the olefin cross-metathesis, Horner-Wadsworth-Emmons (HWE), and Julia-type olefinations, we have established a new protocol for the synthesis of 2a with a substantially improved overall efficiency in terms of the yield (ca. 33%), and diastereo- and E/Z-selectivity. The key transformations were the Evans chiral auxiliary-aided asymmetric allylation for the synthesis of the appropriate chiral intermediates in excellent enantiomeric purity of higher than 97% ee and a modified Julia-Kocienski olefination for the highly selective construction of E-2a with up to 13.6:1 E/Z ratio from the chiral intermediates. Consequently, the results provide an appealing option for the synthesis of aliskiren. This journal is

Conception and evolution of stereocontrolled strategies toward functionalized 8-aryloctanoic acids related to the total synthesis of aliskiren

A detailed account is given describing the approaches used toward the total synthesis of aliskiren. In particular, ring-closing metathesis with the Hoveyda-Grubbs catalyst accelerates the formation of a 9-membered lactone from an (R)-ester. The diastereom

SOLID STATE FORMS OF ALISKIREN COMPOUNDS

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