149709-60-4

Basic information

• Product Name: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoate
• Synonyms: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoate;Ethyl (2R,4S)-4-([1,1'-biphenyl]-4-ylmethyl)-4-[(tert-butoxycarbonyl)amino]-2-methylbutanoate;LCZ702;Ethyl (2R,4S)-5-(4-biphenylyl)-2-methyl-4-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)pentanoate
• CAS NO: 149709-60-4
• Molecular Formula: C₂₅H₃₃NO₄
• Molecular Weight: 411.53382
• EINECS: -0
• Product Categories: LCZ696
• Mol File: 149709-60-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 549.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.066±0.06 g/cm3(Predicted)
• PKA: 12.15±0.46(Predicted)
• CAS DataBase Reference: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoate(149709-60-4)
• EPA Substance Registry System: (2R,4S)-ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpentanoate(149709-60-4)

Safety Data

• Hazardous Substances Data: 149709-60-4(Hazardous Substances Data)

Usage

Description

(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate is a complex organic compound with a specific stereochemistry, characterized by its 2R,4S configuration. It is a derivative of pentanoic acid, featuring a biphenyl group and a tert-butoxycarbonyl-protected amino group, which contributes to its unique chemical properties and potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate is used as a synthetic intermediate for the creation of complex organic molecules. Its versatility in chemical reactions makes it a valuable asset in the synthesis of a wide range of compounds, including those with potential applications in various industries such as pharmaceuticals, materials science, and agrochemicals.
Used in the Synthesis of Sacubitri (S080900):
(2R,4S)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate is specifically used as a building block in the synthesis of Sacubitri (S080900), an antihypertensive drug. Its incorporation into the drug's structure contributes to its efficacy in treating high blood pressure and related cardiovascular conditions.

Upstream product

• 64-17-5 ethanol 
• 98-80-6 phenylboronic acid 
• 162972-36-3 (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino>-N-methoxy-N-metyl<1,1'-biphenyl>-4-propanamide 
• 128779-47-5 (2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 
• 149709-59-1 (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester 
• 149709-58-0 (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal 
• 1426129-50-1 N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester 

Downstream Products

• 149690-12-0 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride 
• 149709-62-6 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 752174-62-2 (2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester 
• 1038924-70-7 (3R,5S)-5-({[1,1'-biphenyl]-4-yl}methyl)-3-methylpyrrolidin-2-one 
• 149690-05-1 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate monosodium salt 

Relevant articles and documents

Preparation method of sacubitril intermediate

The invention provides a preparation method of a sacubitril intermediate. According to the method, 2-bromopropionic acid is used as an initial raw material and reacts with three-level silicon halide under the catalytic action of metal to generate a silicon ylide reagent, compared with a phosphorus ylide reagent, the reaction condition is mild, a hydrogenation reduction reaction can be carried out without alkaline hydrolysis, and ethyl esterification of a SOCl2 catalytic compound III is not influenced. Meanwhile, intramolecular or intermolecular polymerization impurities formed by removal of N protecting groups during ethyl esterification of the compound III can be avoided. The method has the advantages of short preparation process route, low cost, easily available raw materials, high yield and high purity, and is suitable for industrial mass production.

Preparation method for gamma-aminovalerate derivatives

The invention discloses a preparation method for gamma-aminovalerate derivatives. The method comprises the steps of reduction, oxidization, Wittig reaction and hydrogenation reduction with a starting material of N-((tert-butoxycarbonyl)amino-4,4-biphenyl-R-propanoate. The method has the advantages that the process route is short; chiral impurities are reduced by fixing a chiral center in the raw material; oxidized impurities are prevented from being generated by protecting the primary amine; and by using a palladium-charcoal or ruthenium catalyst for assisting a ligand to reduce ethylenic bond, the chiral selectivity is high, the yield is high and the method is suitable for large-scale industrial production.

Novel synthesis method of key component Sacubitril of novel anti-heart-failure drug

The invention discloses a novel synthesis method of key component Sacubitril of a novel anti-heart-failure drug. The method includes transforming a starting material compound 1 to a compound 2; coupling the compound 2 with (1'1)-4-biphenylmagnesium bromide to obtain a compound 3; subjecting the compound 3 to hydrolysis reaction by loading a Boc protecting group, and preparing a compound 5 by means of one-pot reaction; subjecting the compound 5 to Boc group removal and esterification reaction to obtain a compound 6, and reacting the compound 6 with succinic anhydride without separation to obtain a compound 7, namely Sacubitril, wherein the route is as following.