1012341-48-8

Basic information

• Product Name: (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid
• Synonyms: (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid;(2E,4R)-5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-2-Pentenoic acid;5-Biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methyl-pent-2-enoic acid;2-Pentenoic acid, 5-[1,1'-biphenyl]-4-yl-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2-methyl-, (2E,4R)-;(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid###1012341-48-8 enantioMer
• CAS NO: 1012341-48-8
• Molecular Formula: C₂₃H₂₇NO₄
• Molecular Weight: 381.46478
• EINECS: -0
• Product Categories: intermediate;intermediates;LCZ696
• Mol File: 1012341-48-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 595.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.132±0.06 g/cm3(Predicted)
• Vapor Pressure: 8.4-839.931Pa at 20℃
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.67±0.19(Predicted)
• CAS DataBase Reference: (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid(1012341-48-8)
• EPA Substance Registry System: (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid(1012341-48-8)

Safety Data

• Hazardous Substances Data: 1012341-48-8(Hazardous Substances Data)

Usage

Description

(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid is a complex organic compound with a unique molecular structure that features a biphenyl group, a tert-butoxycarbonyl amino group, and a 2-methylpent-2-enoic acid backbone. (R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid is characterized by its specific stereochemistry, with the R and E configurations indicating the spatial arrangement of its atoms.

Uses

Used in Pharmaceutical Industry:
(R,E)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)aMino)-2-Methylpent-2-enoic acid is used as an intermediate in the synthesis of sacubitril, a pharmaceutical compound with angiotensin receptor neprilysin inhibitor (ARNI) properties. It plays a crucial role in the treatment of heart failure by reducing the strain on the heart and improving its function.
In the preparation of sacubitril, this compound is utilized with a Nickel Salt catalyst to facilitate the formation of the desired intermediate. The use of Nickel Salt catalyst enhances the reaction efficiency and selectivity, leading to a more effective and streamlined synthesis process.
The compound's application in the pharmaceutical industry highlights its importance in the development of novel therapeutic agents for various medical conditions, particularly heart failure. Its role in the synthesis of sacubitril demonstrates its potential as a valuable building block in the creation of innovative and effective medications.

Upstream product

• 149709-58-0 (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanal 
• 149818-98-4 methyl (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanoate 
• 1213855-60-7 methyl (R)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 1426129-50-1 N-[(1R)-2-[1,1'-biphenyl]-4-yl-1-(hydroxymethyl)ethyl]carbamic acid tert-butyl ester 
• 1174130-80-3 (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylenepentanoic acid 
• 149709-59-1 ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate 

Downstream Products

• 1012341-50-2 (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid 
• 1012341-54-6 (2S,4S)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpentanoic acid 
• 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 
• 1038924-71-8 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid hydrochloride 

Relevant articles and documents

Method for synthesizing AHU377 calcium salt

The invention discloses a method for synthesizing an AHU377 calcium salt. The method comprises the following steps: reacting 4-bromo-D-phenylalanine with thionyl chloride, reacting obtained methyl 4-bromo-D-phenylalaninate hydrochloride with BOC acid anhydride, reacting the obtained reaction product with phenylmagnesium bromide to obtain N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methylester, reacting the N-tert-butyloxycarbonyl-amino-4,4-biphenyl-R-alanine methyl ester with sodium borohydride, reacting the obtained reaction product with ethyl 2-(triphenylphosphoranylidene)propionate to obtain ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoate, reacting the ethyl (4R)-5-[1,1'-biphenyl]-4-yl-4-[[tert-butoxycarbonyl]amino]-2-methyl-2-pentenoatewith lithium hydroxide, performing catalytic hydrogenation, reacting the obtained catalytic hydrogenation product with thionyl chloride to obtain ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, and stirring and reacting the ethyl (2R, 4S)-5- ([1,1-biphenyl)-4-amino-2-methylpentenoate hydrochloride, calcium chloride and succinic anhydride to obtain the target product.The method has the advantages of simple steps, mild reaction conditions, high purity and high yield.

Preparation method of sacubitril intermediate having low triphenylphosphine oxide content

The invention relates to a preparation method of a sacubitril intermediate having low triphenylphosphine oxide content. The preparation method comprises that water, isopropyl acetate, sodium bromide, sodium bicarbonate and tetramethylpiperidine oxide into (R)-tert-butyl(1-([1, 1'-biphenyl]-4-yl)-3-hydroxypropane-2-yl)carbamate, adding a sodium hypochlorite solution into the mixture drop by drop for a reaction, after the reaction, carrying out layering, taking an organic layer, adding ethoxyformylethylidenetriphenyl phosphorane into the organic layer, after a reaction, concentrating the reaction product, removing isopropyl acetate, adding ethanol, water and lithium hydroxide into the mixture, carrying out heating until reflux, carrying out concentration until drying, adding water and activated carclazyte into the product, carrying out stirring at the room temperature, filtering the mixture, adding ethanol and acetic acid into the filtrate, carrying out heating until reflux, and carrying out cooling and stirring to precipitate solids which are the sacubitril intermediate finished products. The preparation method can reduce triphenylphosphine oxide content of the (R)-tert-butyl(1-([1, 1'-biphenyl]-4-yl)-3-hydroxypropane-2-yl)carbamate.

PROCESS FOR THE PREPARATION OF INTERMEDIATES FOR THE MANUFACTURE OF NEP INHIBITORS

The invention relates to a new process for producing useful intermediates for the manufacture of NEP inhibitors or prodrugs thereof, in particular NEP inhibitors comprising a γ-amino-δ-biphenyl-α-methylalkanoic acid, or acid ester, backbone, such as N-(3-carboxyl-1-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methyl butanoic acid ethyl ester or salt thereof.