137864-24-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride is used as a chemical intermediate for the development of new pharmaceuticals targeting specific receptors or biological pathways. Its unique structure, including the cyanobiphenyl group and benzyl ester moiety, may provide novel interactions with biological targets, potentially leading to the creation of more effective and selective drugs.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride serves as a valuable compound for studying the structure-activity relationships of drug candidates. Its synthesis and modification can provide insights into the design of more potent and selective drugs, contributing to the advancement of medicinal chemistry.
Used in Drug Synthesis and Design:
(S)-2-[(2'-cyanobiphenyl-4-ylmethyl)amino]-3-methylbutyric acid benzyl ester hydrochloride is utilized as a key building block in the synthesis of complex drug molecules. Its unique structural features can be exploited to create new drugs with improved pharmacological properties, such as enhanced efficacy, selectivity, and reduced side effects.

Upstream product

• 16652-76-9 L-valine benzyl ester p-toluenesulfonate salt 
• 114772-54-2 4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile 
• 21760-98-5 L-valine benzyl ester 
• 2042-37-7 o-cyanobromobenzene 
• 114772-53-1 2-Cyano-4'-methylbiphenyl 

Downstream Products

• 137863-20-8 (S)-N-(1-benzyloxycarbonyl-2-methyl-prop-1-yl)-N-pentanoyl-N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amine 
• 137862-53-4 N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine 
• 137864-23-4 (S)-N-[(2'-Cyano-biphenyl-4-yl)methyl]valine benzyl ester 

Relevant academic research and scientific papers

Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan

An efficient continuous flow process for the synthesis of 5-substituted 1H-tetrazoles is described. The process involves the reaction between a polymer-supported triorganotin azide and organic nitriles. The polymer-supported organotin azide, which is in situ generated with a polystyrene-supported triorganotin alkoxide and trimethylsilylazide, is immobilized in a packed bed reactor. This approach is simple, fast (it takes from 7.5 to 15 min), and guarantees a low concentration of tin residues in the products (5 ppm). The process was developed to aryl-, heteroaryl-, and also alkylnitriles and was applied for the synthesis of valsartan, an angiotensin II receptor antagonist.

PROCESS FOR PREPARATION OF VALSARTAN INTERMEDIATE

The present invention provides a process for preparation of a key intermediate of valsartan in a pure form and use of this intermediate for the preparation of valsartan or a pharmaceutically acceptable salt in pure form.

PROCESSES FOR THE PREPARATION OF INTERMEDIATES OF VALSARTAN

The present invention relates to processes for the preparation of intermediates of valsartan.

Processes for the preparation of intermediates of valsartan

The present invention relates to processes for the preparation of intermediates of valsartan.

A high-throughput process for valsartan

With the redesign of three chemical steps, the throughput of the valsartan manufacturing process could be significantly increased, and with the substitution of chlorobenzene with cyclohexane in the bromination of 4′-methyl-biphenyl-2-carbonitrile (6) to 4′bromomethyl-biphenyl-2- carbonitrile (5), halogenated solvents are no longer used in the whole valsartan production process. The alkylation of (S)-2-amino-3-methyl-butyric acid benzyl ester (8) with 4′-bromomethyl-biphenyl-2-carbonitrile (5), and the acylation of(S)-2-[(2′-cyano-biphenyl-4-ylmethyl)-amino]-3-methyl-butyric acid benzyl ester (4) to (S)-2-[(2′-cyano-biphenyl-4-ylmethyl)-pentanoyl- amino]-3-methyl-butyric acid benzyl ester (3) were thoroughly modified. In the acylation of 4 to 3, N-ethyldiisopro-pylamine was replaced by aqueous sodium hydroxide by using the conditions of the Schotten-Baumann reaction, leading to a better quality of intermediate 3. In the alkylation of 8 with 5, N-ethyldiisopropylamine was indirectly replaced by aqueous sodium hydroxide. The reaction runs under homogenous conditions with (S)-2-amino-3-methyl-butyric acid benzyl ester (8) acting as acceptor for hydrobromic acid; recycling of 8 is performed by extraction with aqueous sodium hydroxide.

Process for the Preparation of Valsartan and its Intermediates

The present invention concerns a process for preparing valsartan of Formula I: comprising purifying intermediate benzyl valsartan of Formula IV by crystallizing said benzyl valsartan of lower purity from a first solvent which is a ternary mixture comprising a hydrophilic solvent, a non-polar protic solvent and water; recovering benzyl valsartan from said ternary mixture followed by crystallizing benzyl valsartan from a second solvent comprising a non-polar aprotic solvent or polar aprotic solvent or their mixture; and recovering benzyl valsartan substantially free of organotin impurity; and converting said benzyl valsartan of into valsartan

Process for the preparation of valsartan and its intermediates

The present invention relates to an improved process for the preparation of valsartan and its intermediates in substantially pure enantiomeric form. In particular, the present invention provides a process for preparing benzyl valsartan intermediate substantially free of organotin impurities. The valsartan produced from such benzyl valsartan intermediate requires significantly lower catalyst loading and has superior purity.