57292-44-1

Basic information

• Product Name: BOC-D-4-Chlorophe
• Synonyms: BOC-D-PHE(4-CL)-OH;BOC-D-PHE(PCL)-OH;BOC-4-CHLORO-D-PHENYLALANINE;BOC-4-CHLORO-D-PHE-OH;BOC-D-4-CHLOROPHE;BOC-D-4-CHLOROPHENYLALANINE;BOC-P-CHLORO-D-PHENYLALANINE;BOC-P-CHLORO-D-PHE-OH
• CAS NO: 57292-44-1
• 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: 57292-44-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: ~110 °C
• Boiling Point: 452.5 °C at 760 mmHg
• Flash Point: 227.5 °C
• Appearance: White/Powder
• Density: 1.2167 (rough estimate)
• Vapor Pressure: 5.61E-09mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: Store at RT.
• PKA: 3.83±0.10(Predicted)
• BRN: 5381988
• CAS DataBase Reference: BOC-D-4-Chlorophe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-4-Chlorophe(57292-44-1)
• EPA Substance Registry System: BOC-D-4-Chlorophe(57292-44-1)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 57292-44-1(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

N-(tert-Butoxycarbonyl)-D-4-chlorophenylalanine, is one of the phenylalanine derivatives, that can be used for the synthesis of THIQ (C380165), which is a selective melanocortin 4 receptor.

InChI:InChI=1/C14H18ClNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 7424-00-2 DL-Phe(4Cl) 
• 139377-27-8 (R)-2-Azido-3-(4-chloro-phenyl)-propionic acid 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 1027659-22-8 C₁₄H₁₇ClO₃ 
• 14091-08-8 para-Chloro-D-phenylalanine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 14173-39-8 p-chlorophenylalanine 
• 68759-85-3 para-chlorophenylalanine methyl ester 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 77-92-9 citric acid 
• 159750-01-3 (4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 159750-02-4 (4S,2S)-4-Chloro-<2-azido-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 

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 
• 74105-22-9 t-butyloxycarbonyl-4-chlorophenylalanyl-serine methyl ester 
• 119744-86-4 tert-butyl (S)-[1-amino-3-(4-chlorophenyl)-1-oxopropan-2-yl]carbamate 
• 84796-24-7 tert-butyloxycarbonyl-p-chlorophenylalanyl-isoleucyl-glutaminyl-asparaginyl-S-(β-carboxyethyl)homocysteinyl-prolyl-leucyl-glycine amide 
• 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 
• 139377-30-3 D-(-)-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl 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.

New reagent for the introduction of Boc protecting group to amines: Boc-OASUD

A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD, being a solid and more stable, is a better alternative to di-tert-butyl dicarbonate which is low melting and has to be dispensed in plastic containers than glass because of its poor stability.