51301-86-1

Basic information

• Product Name: 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID
• Synonyms: BOC-DL-4-CHLOROPHENYLALANINE;2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID;Boc-4-Chloro-DL-Phenylalanine;Boc-DL-Phe(4-Cl)-OH;N-(tert-Butoxycarbonyl)-4-chloro-DL-phenylalanine;2-BOC-AMINO-3-(4-CHLORO-PHENYL)-PROPANOIC ACID
• CAS NO: 51301-86-1
• Molecular Formula: C₁₄H₁₈ClNO₄
• Molecular Weight: 299.75
• Mol File: 51301-86-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID(51301-86-1)
• EPA Substance Registry System: 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID(51301-86-1)

Safety Data

• Hazardous Substances Data: 51301-86-1(Hazardous Substances Data)

Usage

Description

2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID is a chemical compound characterized by its unique molecular structure, which features a tert-butoxycarbonyl group, an amino group, a 4-chlorophenyl group, and a propionic acid moiety. 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID is known for its distinct properties and potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID is used as an analyte in the enantiomeric separation process for pharmaceutical applications. 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID plays a crucial role in the development and analysis of chiral drugs, which are essential in the pharmaceutical industry due to their different biological activities and potential therapeutic benefits.
Used in Analytical Chemistry:
In the field of analytical chemistry, 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID is utilized as an analyte for enantiomeric separation by High-Performance Liquid Chromatography (HPLC). This technique is vital for determining the purity and enantiomeric composition of chiral compounds, which is essential for understanding their properties and potential applications.
Used in Chiral Stationary Phase Development:
2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID is also used in the development of chiral stationary phases for HPLC. 2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID's interaction with covalently bonded macrocyclic antibiotic ristocetin A as a chiral stationary phase helps in the separation of enantiomers, which is a critical aspect of chiral chromatography and has significant implications in various industries, including pharmaceuticals, agrochemicals, and environmental science.

Upstream product

• 68759-85-3 para-chlorophenylalanine methyl ester 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 7424-00-2 DL-Phe(4Cl) 
• 77-92-9 citric acid 
• 159750-01-3 (4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 
• 1027659-22-8 C₁₄H₁₇ClO₃ 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 159750-02-4 (4S,2S)-4-Chloro-<2-azido-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 
• 14173-39-8 p-chlorophenylalanine 
• 159750-06-8 (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 172035-51-7 (9S,12S,15S)-12-Benzyl-15-tert-butoxycarbonylamino-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester 
• 371111-92-1 [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid 
• 1310688-53-9 C₁₃H₂₀ClN₃O 
• 1310688-54-0 C₁₄H₂₀ClN₃O 
• 1310688-56-2 C₁₇H₂₄ClN₃O 
• 1310801-00-3 C₁₇H₂₄ClN₃O 
• 1310687-65-0 C₃₁H₃₇ClN₄O₂ 
• 1310687-66-1 C₃₂H₃₉ClN₄O₂ 
• 1310687-67-2 C₂₇H₃₉ClN₄O₄S 
• 1310687-68-3 C₂₉H₄₃ClN₄O₄S 
• 1310687-69-4 C₃₀H₄₅ClN₄O₄S 
• 1310687-70-7 C₃₀H₄₅ClN₄O₄S 
• 1310687-71-8 C₂₀H₂₅ClN₂O₄S 
• 1310687-72-9 C₂₆H₂₉ClN₂O₄S 

Relevant articles and documents

SUBSTITUTED AMINO TRIAZOLES USEFUL AS CHITINASE INHIBITORS

Disclosed are amino triazole compounds of formula (I). These compounds are inhibitors of acidic mammalian chitinase and chitotriosidase. Also disclosed are methods of using the compounds to treat asthma reactions caused by allergens, as well as acute and chronic inflammatory diseases, autoimmune diseases, dental diseases, neurologic diseases, metabolic diseases, liver diseases, polycystic ovary syndrome, endometriosis, and cancer.

Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome

A series of tripeptidic proteasome inhibitors with furylketone as C-terminus were designed and synthesized. Biochemical evaluations against β1, β2 and β5 subunits revealed that they acted selectively on β5 subunit with IC50s against chymotrypsin-like (CT-L) activity in micromolar range. LC-MS/MS analysis of the ligand-20S proteasome mixture showed that the most potent compound 11m (IC50 = 0.18 μM) made no covalent modification on 20S proteasome. However, it was identified acting in a slowly reversible manner in wash-out assay and the reversibility was much lower than that of MG132, suggesting the possibility of these tripeptidic furylketones forming reversible covalent bonds with 20S proteasome. Several compounds were selected for anti-proliferative assay towards multiple cancer cell lines, and compound 11m displayed comparable potency to positive control (MG132) in all cell lines tested. Furthermore, the pharmacokinetic (PK) data in rats indicated 11m behaved similarly (Cmax, 2007 μg/L; AUC0?t, 680 μg/L·h; Vss, 0.66 L/kg) to the clinical used agent carfilzomib. All these data suggest 11m is a good lead compound to be developed to novel anti-tumor agent.

Synthesis of an amidosulfonate-tagged biphenyl phosphine and its application in the Suzuki-Miyaura reaction affording biphenyl-substituted amino acids in water

An amidosulfonate-tagged phosphinobiphenyl, viz triethylammonium 2-(dicyclohexylphosphino)-4′-{[(sulfonatomethyl)amino]carbonyl}biphenyl (3), was prepared in two steps from 2-(dicyclohexylphosphino)biphenyl-4′-carboxylic acid and fully characterized including the crystal structure determination. As a highly polar phosphine ligand, compound 3 was employed in the Pd-catalyzed Suzuki-Miyaura cross-coupling of N-Boc protected 4-bromo and 4-chlorophenylalanine with aromatic boronic acids to afford the corresponding biphenyls in aqueous N,N-dimethylformamide or pure water. The coupling was demonstrated to proceed very well and without the loss of the Boc protecting group when the bromo-substituted substrate is reacted in the presence of 1 mol.% of Pd/3 catalyst in water at 40 °C. Reactions with boronic acids bearing electron-withdrawing substituents and, mainly, those with the less reactive chlorophenylalanine substrate required slightly higher reaction temperature and more catalyst to achieve similar results.