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

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

Uses

Used in Pharmaceutical Industry:
BOC-D-4-Chlorophe is used as a key intermediate in the synthesis of THIQ (C380165) for its role as a selective melanocortin 4 receptor. This application is significant due to the potential therapeutic benefits of targeting melanocortin 4 receptors, which are involved in various physiological processes, including energy balance, sexual behavior, and pigmentation.
Additionally, as a phenylalanine derivative, BOC-D-4-Chlorophe may have other applications in the development of novel pharmaceutical compounds, leveraging its unique chemical properties to target specific biological pathways or receptors.

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) 
• 1027659-22-8 C₁₄H₁₇ClO₃ 
• 139377-25-6 (4R,5S)-4-chloro-1-<3-oxo-3-(2-oxo-4-methyl-5-phenyl-3-oxazolidinyl)propyl>benzene 
• 139377-26-7 (4R,5S,2R)-4-chloro-1-<2-azido-3-oxo-3-(2-oxo-4-methyl-5-phenyl-3-oxazolidinyl)propyl>benzene 
• 123795-38-0 methyl (R)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoate 
• 14091-08-8 para-Chloro-D-phenylalanine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 14173-39-8 p-chlorophenylalanine 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 159750-01-3 (4S)-4-Chloro-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 
• 77-92-9 citric acid 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 139377-27-8 (R)-2-Azido-3-(4-chloro-phenyl)-propionic acid 

Downstream Products

• 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 
• 139377-30-3 D,L-N-<(1,1-dimethylethoxy)carbonyl>-4-chlorophenylalanine 2-bromoethyl ester 
• 909110-56-1 2-(benzhydrylidene-amino)-3-(4-chloro-phenyl)-propionic acid allyl ester 
• 862010-81-9 [1-(3-{4-chloro-2-[3-(5-cyano-pyridin-2-yl)-ureido]-phenoxy}-propylcarbamoyl)-2-(4-chloro-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 182492-20-2 N-tert-butyloxycarbonyl-N-methyl-4-chlorophenylalanine methyl ester 
• 1239902-81-8 C₂₀H₂₂BrClN₂O₃ 
• 1187387-40-1 (+/-)-tert-butyl 1-[allyl-(benzyl)amino]-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate 
• 1310687-78-5 C₂₅H₃₀ClN₃O₂ 
• 1310687-79-6 C₂₅H₂₉Cl₂N₃O₂ 
• 1310687-81-0 C₂₅H₂₉Cl₂N₃O₂ 
• 1310687-83-2 C₂₅H₂₉Cl₂N₃O₂ 
• 1310687-84-3 C₂₅H₂₈Cl₃N₃O₂ 
• 1310687-85-4 C₂₅H₂₈Cl₃N₃O₂ 

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.

Discovery of OATD-01, a First-in-Class Chitinase Inhibitor as Potential New Therapeutics for Idiopathic Pulmonary Fibrosis

Chitotriosidase (CHIT1) and acidic mammalian chitinase (AMCase) are the enzymatically active chitinases that have been implicated in the pathology of chronic lung diseases such as asthma and interstitial lung diseases (ILDs), including idiopathic pulmonary fibrosis (IPF) and sarcoidosis. The clinical and preclinical data suggest that pharmacological inhibition of CHIT1 might represent a novel therapeutic approach in IPF. Structural modification of an advanced lead molecule 3 led to the identification of compound 9 (OATD-01), a highly active CHIT1 inhibitor with both an excellent PK profile in multiple species and selectivity against a panel of other off-targets. OATD-01 given orally once daily in a range of doses between 30 and 100 mg/kg showed significant antifibrotic efficacy in an animal model of bleomycin-induced pulmonary fibrosis. OATD-01 is the first-in-class CHIT1 inhibitor, currently completed phase 1b of clinical trials, to be a potential treatment for IPF.

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.

SUBSTITUTED AMINO TRIAZOLES USEFUL AS HUMAN CHITINASE INHIBITORS

Disclosed are amino triazole compounds substituted with a piperidinyl ring that is itself substituted with a heterocyclic ring. 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.

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.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

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.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Collection of traceable compounds and uses thereof

The use of a collection of compounds of general formula (I), wherein: n is 0 or 1; p represents an integer between 1 and 6; r represents an integer between 1 and 12; R1 and R′1 represent in particular a hydrogen atom; R2 represents an amino acid side chain or an amino acid derivative; R3 represents a group derived from a carboxylic acid, bearing a basic entity; R4 represents in particular an alkyl group containing 1 to 10 carbon atoms; and A represents a hydrogen atom, a protecting group or a tracing group, in particular a fluorophor, a coloring agent or a quencher, for determining, through binding studies, ligands of receptors whose ligand is unknown or whose ligand useful for carrying out specific affinity binding assays is unknown.

Discovery of pyrrolopyrimidine inhibitors of Akt

The discovery and optimization of a series of pyrrolopyrimidine based protein kinase B (Pkb/Akt) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent inhibition of all three Akt isoforms and knockdown of phospho-PRAS40 levels in LNCaP cells and tumor xenografts.