137255-86-8

Usage

Uses

Used in Pharmaceutical Industry:
(S)-METHYL N-TERT-BUTOXYCARBONYL-3-(4-BIPHENYLYL)-2-AMINOPROPIONATE is used as a building block in organic synthesis and peptide chemistry for the development of new drugs and medications. Its role in the synthesis of peptides and peptidomimetics makes it a valuable component in the creation of innovative pharmaceutical compounds.

InChI:InChI=1/C21H25NO4/c1-21(2,3)26-20(24)22-18(19(23)25-4)14-15-10-12-17(13-11-15)16-8-6-5-7-9-16/h5-13,18H,14H2,1-4H3,(H,22,24)/t18-/m0/s1

Upstream product

• 112766-18-4 methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate 
• 98-80-6 phenylboronic acid 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 69942-12-7 N-tert-butoxycarbonylserine methyl ester 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 175844-11-8 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 113850-76-3 N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester 
• 591-50-4 iodobenzene 

Downstream Products

• 139040-51-0 methyl (S)-2-amino-3-(biphenyl-4-yl)propanoate 
• 149709-63-7 sacubitril 
• 149709-63-7 4-(((2S,4R)-1-([1,1'-biphenyl]-4-yl)-5-ethoxy-4-methyl-5-oxopentan-2-yl)amino)-4-oxobutanoic acid 
• 766480-48-2 (R)-5-Biphenyl-4-yl-4-(3-carboxy-propionylamino)-2-methyl-pentanoic acid ethyl ester 
• 753421-85-1 (R)-4-Amino-5-biphenyl-4-yl-2-methyl-pentanoic acid ethyl ester 
• 119273-61-9 N-tert-butoxycarbonyl-p-phenyl-L-phenylalanine 
• 63024-30-6 (S)-2-amino-3-(biphenyl-4-yl)-propionic acid methyl ester hydrochloride 

Relevant academic research and scientific papers

Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis

We describe herein a two-step process for the conversion of serine to a wide array of optically pure unnatural amino acids. This method utilizes a photocatalytic cross-electrophile coupling between a bromoalkyl intermediate and a diverse set of aryl halides to produce artificial analogues of phenylalanine, tryptophan, and histidine. The reaction is tolerant of a broad range of functionalities and can be leveraged toward the scalable synthesis of valuable pharmaceutical scaffolds via flow technology.

Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates

While phenols are frequent and convenient aryl sources in cross-coupling, typically as sulfonate esters, the direct cross-Ullmann coupling of two different sulfonate esters is unknown. We report here a general solution to this challenge catalyzed by a combination of Ni and Pd with Zn reductant and LiBr as an additive. The reaction has broad scope, as demonstrated in 33 examples (65% ± 11% average yield). Mechanistic studies show that Pd strongly prefers the aryl triflate, the Ni catalyst has a small preference for the aryl tosylate, aryl transfer between catalysts is mediated by Zn, and Pd improves yields by consuming arylzinc intermediates.

SUBSTITUTED HETEROCYCLIC COMPOUNDS

The present invention relates to substituted heterocyclic compounds of Formula I or XI: or pharmaceutically acceptable salts or N-oxides or quaternary ammonium salts thereof wherein constituent members are provided hereinwith, as well as their compositions and methods of use, which are histamine II4 receptor inhibitors useful in the treatment of histamine II4 receptor-associated conditions or diseases or disorders including, for example, inflammatory diseases or disorders, pruritus, and pain.

Chiral monomers with minimal functional group linkages for suspension co-polymerization: A Suzuki coupling approach

A new strategy for the synthesis of chiral monomers for co-polymerization with styrene is described. Suzuki coupling of 4-vinylphenylboronic acid with chiral aryl triflates 5 and 13, and subsequent elaboration has resulted in chiral monomers 9 and 10. One of these monomers 10 has subsequently been incorporated into a polystyrene gel-type resin 16 with a functional group loading of 0.48 mmolg-1.

A new approach for modification of phenylalanine peptides by Suzuki-Miyaura coupling reaction.

For the first time, we have modified phenylalanine peptides by the Suzuki-Miyaura coupling reaction which may be useful in developing combinatorial libraries of peptidomimetics.

An efficient synthesis of 4-aryl and 4-vinylphenylalanines by stille cross-coupling reaction

The palladium-catalyzed reaction of N-Boc-4-trimethylstannyl-L-phenylalanine methyl ester (1) with a variety of aryl and vinyl iodides and triflates (2) affords the corresponding 4-aryl and 4-vinylphenylalanines 3 in synthetically useful yields.

Dicarboxylic Acid Dipeptide Neutral Endopeptidase Inhibitors

The synthesis of three series of dicarboxylic acid dipeptide neutral endopeptidase 24.11 (NEP) inhibitors is described.In particular, the amino butyramide 21a exhibited potent NEP inhibitory activity (IC50 = 5.0 nM) in vitro and in vivo.Blood levels of 21a were determined using an ex vivo method by measuring plasma inhibitory activity in conscious rats, mongrel dogs, and cynomolgus monkeys.Free drug concentrations were 10-1500 times greater than the inhibitory constant for NEP over the course of a 6 h experiment.A good correlation of free drug concentrations was obtained when comparing values determined by the ex vivo analysis to those calculated from direct HPLC measurements.Plasma atrial natriuretic factor (exogenous) levels were elevated in rats and dogs after oral administration of 19a.Urinary volume and urinary sodium excretion were also potentiated in anesthetized dogs treated with 21a.

Phosphono/biaryl substituted dipetide derivatives

The invention relates to the N-phosphonomethyl-biaryl substituted dipeptide derivatives of formula I STR1 and tetrazole derivatives of the formula Ia STR2 wherein A represents a direct bond, lower alkylene, phenylene or cyclohexylene; m represents 1 or zero, provided that m represents 1 when A is a direct bond; R2 represents hydrogen, hydroxy, lower alkyl, aryl-lower alkyl, C5 -C7 -cycloalkyl-lower alkyl, amino-lower alkyl, hydroxy-lower alkyl, lower alkylthio-lower alkyl, lower alkoxy-lower alkyl, aryl-lower alkylthio-lower alkyl or aryl-lower alkoxy-lower alkyl; biaryl represents phenyl substituted by carbocyclic or heterocyclic aryl; and pharmaceutically acceptable mono-, di- or tri-ester derivatives thereof in which one, two or three of the acidic hydroxy groups of the carboxyl and/or phosphono functional groups are esterified in form of a mono-, di- or tri-pharmaceutically acceptable ester; and pharmaceutically acceptable amide derivatives thereof wherein the carboxyl group is derivatized in form of a pharmaceutically acceptable amide; and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising said compounds; methods for the preparation of said compounds and for the preparation of intermediates; and methods of treating disorders in mammals which are responsive to the inhibition of neutral endopeptidases by administration of said compounds to mammals in need of such treatment.

Phosphono/biaryl substituted dipeptide derivatives

The invention relates to the N-phosphonomethyl-biaryl substituted dipeptide derivatives of formula I STR1 wherein A represents a direct bond, lower alkylene, phenylene or cyclohexylene; m represents 1 or zero, provided that m represents 1 when A is a direct bond; R2 represents hydrogen, hydroxy, lower alkyl, aryl-lower alkyl, C5 -C7 -cycloalkyl-lower alkyl, amino-lower alkyl, hydroxyl-lower alkyl, lower alkylthio-lower alkyl, lower alkoxy-lower alkyl, aryl-lower alkylthio-lower alkyl or aryl-lower alkoxy-lower alkyl; biaryl represents phenyl substituted by carbocyclic or heterocyclic aryl; and pharmaceutically acceptable mono-, di- or tri-ester derivatives thereof in which one, two or three of the acidic hydroxy groups of the carboxyl and phosphono functional groups are esterified in form of a mono-, di- or tri- pharmaceutically acceptable ester; and pharmaceutically acceptable amide derivatives thereof wherein the carboxyl group is derivatized in form of a pharmaceutically acceptable amide; and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising said compounds; methods for the preparation of said compounds and for the preparation of intermediates; and methods of treating disorders in mammals which are responsive to the inhibition of neutral endopeptidases by administration of said compounds to mammals in need of such treatment.