68090-88-0

Basic information

• Product Name: BOC-L-4-Chlorophe
• Synonyms: N-TERT-BUTOXYCARBONYL-4-CHLOROPHENYL-L-ALANINE;N-ALPHA-T-BUTOXYCARBONYL-(4-CHLOROPHENYL)-L-ALANINE;N-ALPHA-T-BOC-4-CHLORO-L-PHENYLALANINE;N-ALPHA-TERT-BUTYLOXYCARBONYL-4-CHLORO-L-PHENYLALANINE;N-ALPHA-T-BUTOXYCARBONYL-P-CHLORO-L-PHENYLALANINE;RARECHEM BK PT 0014;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(4-CHLORO-PHENYL)-PROPIONIC ACID;(S)-N-BOC-4-CHLOROPHENYLALANINE
• CAS NO: 68090-88-0
• Molecular Formula: C₁₄H₁₈ClNO₄
• Molecular Weight: 299.75
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Phenylalanine [Phe, F];Unusual Amino Acids;Boc-Amino acid series;a-amino
• Mol File: 68090-88-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: ~110 °C
• Boiling Point: 452.5 °C at 760 mmHg
• Flash Point: 227.5 °C
• Appearance: pale yellow granular powder
• Density: 1.2167 (rough estimate)
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: Store at RT.
• PKA: 3.83±0.10(Predicted)
• BRN: 4261946
• CAS DataBase Reference: BOC-L-4-Chlorophe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-4-Chlorophe(68090-88-0)
• EPA Substance Registry System: BOC-L-4-Chlorophe(68090-88-0)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 68090-88-0(Hazardous Substances Data)

Usage

Chemical Properties

pale yellow granular powder

Uses

BOC-4-chlorophenylalanine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 14173-39-8 p-chlorophenylalanine 
• 159750-02-4 (4S,2S)-4-Chloro-<2-azido-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 
• 68759-85-3 para-chlorophenylalanine methyl ester 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 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 
• 159750-06-8 (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

• 159750-10-4 N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylaanine 2-iodoethyl ester 
• 139377-29-0 D,L-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-(trimethylsilyl)ethyl ester 
• 139377-31-4 D,L-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine pentafluorophenyl ester 
• 119744-86-4 tert-butyl (S)-[1-amino-3-(4-chlorophenyl)-1-oxopropan-2-yl]carbamate 
• 139377-30-3 D,L-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester 
• 159750-09-1 N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester 
• 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 
• 169499-14-3 N-(Boc-p-chloro-L-phenylalanyl)morpholine 
• 251309-03-2 2-[(S)-2-(4-Chloro-benzyl)-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-N-((S)-1-{(S)-1-[imino-(2,2,5,7,8-pentamethyl-chroman-6-sulfonylamino)-methyl]-piperidin-3-ylmethyl}-2-oxo-2-thiazol-2-yl-ethyl)-acetamide 
• 251308-75-5 [2-(4-chloro-benzyl)-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetic acid tert-butyl ester 
• 14173-40-1 (S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride 
• 251308-88-0 [(S)-2-(4-Chloro-benzyl)-3,6-dioxo-4-(3-phenyl-propyl)-piperazin-1-yl]-acetic acid 
• 1393911-89-1 C₂₆H₂₆ClN₃O₃S 
• 251308-48-2 [[(S)-2-Amino-3-(4-chloro-phenyl)-propionyl]-(3-phenyl-propyl)-amino]-acetic acid methyl ester 

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.