149709-58-0

Basic information

• Product Name: ((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester
• Synonyms: ((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester;(R)-tert-butyl (1-([1,1'-biphenyl]-4-yl)-3-oxopropan-2-yl)carbamate;[(1R)-2-(Biphenyl-4-yl)-1-formylethyl]carbamic acid tert-butyl ester;((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl este
• CAS NO: 149709-58-0
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.40152
• EINECS: -0
• Product Categories: LCZ696
• Mol File: 149709-58-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 475.1±45.0 °C(Predicted)
• Appearance: /
• Density: 1.097±0.06 g/cm3(Predicted)
• PKA: 11.17±0.46(Predicted)
• CAS DataBase Reference: ((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: ((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester(149709-58-0)
• EPA Substance Registry System: ((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester(149709-58-0)

Safety Data

• Hazardous Substances Data: 149709-58-0(Hazardous Substances Data)

Usage

Description

((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester, also known as LCZ696 (L270005) impurity, is a chemical compound derived from the synthesis of a novel dual-acting inhibitor of angiotensin II receptor and neprilysin. It possesses structural characteristics that allow it to interact with specific biological targets, making it a potential candidate for pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
((R)-2-biphenyl-4-yl-1-forMylethyl)carbaMic acid t-butyl ester is used as an impurity in the development of LCZ696 (L270005), a novel dual-acting inhibitor of angiotensin II receptor and neprilysin. It plays a role in blood pressure reduction, which is essential for managing hypertension and related cardiovascular conditions.
The compound's involvement in the development of LCZ696 highlights its potential application in the pharmaceutical industry, particularly in the treatment of hypertension and other related conditions. Its presence as an impurity in the synthesis process may also warrant further investigation into its potential effects on the overall efficacy and safety of the drug.

Upstream product

• 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 
• 24424-99-5 di-tert-butyl dicarbonate 
• 62561-75-5 (R)-2-amino-3-(4-iodophenyl)propanoic acid 
• 673-06-3 D-(R)-phenylalanine 
• 1383027-39-1 C₁₇H₂₃F₃N₂O₇S 
• 929872-80-0 tert-butyl (R)-3-(4-hydroxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-ylcarbamate 
• 70642-86-3 N-(tert-butoxycarbonyl)-D-tyrosine 
• 149709-56-8 methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-D-tyrosinate 
• 149818-98-4 methyl (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino><1,1'-biphenyl>-4-propanoate 
• 76757-90-9 N-(tert-butoxycarbonyl)-D-tyrosine methyl ester 
• 128779-47-5 (2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 
• 162972-36-3 (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino>-N-methoxy-N-metyl<1,1'-biphenyl>-4-propanamide 

Downstream Products

• 149709-59-1 ethyl 5-(4-<1,1'-biphenyl>yl)-4-<<(1,1-dimethylethoxy)carbonyl>amino>-2-methyl-2-pentenoate 
• 753421-85-1 ethyl (γS)-γ-amino-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-63-7 α-ethyl (γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-63-7 α-ethyl (αS,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-62-6 α-ethyl (αR,γS)-γ-<(3-carboxy-1-oxopropyl)amino>-α-methyl<1,1'-biphenyl>-4-pentanoate 
• 149709-59-1 (R)-5-biphenyl-4-yl-4-tert-butoxycarbonylamino-2-methylpent-2-enoic acid ethyl ester 
• 149709-60-4 ethyl (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-((tert-butoxycarbonyl)amino)-2-methylpentanoate 
• 149690-12-0 (2R,4S)-5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoic acid ethyl ester hydrochloride 
• 752174-62-2 (2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester 
• 1012341-48-8 (2E,4R)-5-{[1,1'-biphenyl]-4-yl}-4-{[(tert-butoxy)carbonyl]amino}-2-methylpent-2-enoic acid 
• 1012341-50-2 (2R,4S)-5-[(1,1‘-biphenyl)-4-yl]-4-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid 

Relevant articles and documents

Synthesis method of sacubitril drug intermediate

The invention relates to the technical field of synthesis of medical intermediates, in particular to a synthesis method of a sacubitril drug intermediate. The synthesis method comprises the followingsynthesis route: under the protection of nitrogen, adding a compound II and a solvent into a reaction flask, stirring to dissolve, adding diisobutylaluminum hydride according to the feeding molar ratio of compound II to diisobutylaluminum hydride (DIBAH) of 1: (1-2), and controlling the temperature, stirring for reaction, and monitoring the reaction by TLC; after the reaction is finished, adding aKHSO4/water solution for quenching reaction; combining the obtained solution with a 1N HCl solution, stirring for 5 minutes, and separating an organic phase; extracting the aqueous phase with EtOAc,combining the organic phases, drying with anhydrous sodium sulfate, and concentrating to dryness to obtain a compound I; according to the invention, diisobutylaluminum hydride is selected to replace lithium aluminum hydride which is easy to explosively decompose when encountering water. The method is simple in reaction operation, high in yield and suitable for industrial large-scale production.

Preparation method of N-Boc biphenyl alaninal

The invention discloses a preparation method of N-Boc-biphenyl alaninal, and the preparation method comprises the following steps: the N-Boc-biphenyl alaninal can be obtained by oxidation reaction of N-Boc-biphenyl alaninol and 2-iodoxybenzoic acid in an organic solvent. The method has the advantages of simple operation, high yield, high purity, low cost and little pollution, and is suitable for industrial production.

Method for preparing LCZ-696 key intermediate

The invention relates to a method for preparing an LCZ-696 key intermediate, and aims to provide a novel method for preparing the LCZ-696 key intermediate. The LCZ-696 key intermediate has high yield, high impurity and low requirement for production equipment and is easy for industrialized production. The method includes the following steps: 1, adding NaHCO3 in water, conducting stirring and dissolving until the obtained aqueous solution is clarified, cooling the NaHCO3 aqueous solution to 10-20 DEG C, maintaining the temperature constant, and dropwise adding a NaClO solution to the NaHCO3 aqueous solution; 2, adding isopropyl acetate, a compound I and NaBr successively into a reaction kettle, conducting stirring at 20-35 DEG C for 20-40min for sufficiently dissolving, and adding TEMPO; 3, rapidly and dropwise adding the NaHCO3-NaClO aqueous solution in the compound I-NaBr-TEMPO isopropyl acetate solution obtained in step 2, purifying a compound II, and then preparing a compound IV. The method has the advantages that the yield of the compound IV is increased to 80% or above from about 50% in the prior art, the content of impurities is reduced, the purity of the prepared product reaches 99.0% or above, and thus the prepared product can be directly used in a following reaction without being purified. Moreover, the reaction temperature can be controlled in the range of 10 to 35 DEG C, the requirements for industrial equipment and operation time are reduced, and industrial production is thus greatly facilitated.