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

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

Uses

Used in Pharmaceutical Industry:
BOC-L-4-Chlorophe is used as a key building block for the synthesis of peptides, which are essential in the development of peptide-based drugs. Its unique chemical properties allow for the creation of a wide range of therapeutic peptides with diverse applications.
Used in Peptide Drug Market:
BOC-L-4-Chlorophe is used as a crucial component in the fast and reliable synthesis of peptides, catering to the growing demand for peptide-based drugs in the pharmaceutical market. Its versatility and chemical stability contribute to the efficient production of high-quality peptide drugs.
Used in Research and Development:
BOC-L-4-Chlorophe is used as a research tool for studying the structure, function, and interactions of peptides in various biological systems. Its unique properties make it an invaluable asset in advancing scientific understanding and driving innovation in the field of peptide research.

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

• 847056-54-6 (S)-2-tert-Butoxycarbonylamino-3-(4-chloro-phenyl)-propionic acid (3aR,4R,6R,6aR)-6-(2-bromo-5,6-dichloro-benzoimidazol-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 928342-09-0 Boc-Trp-(p-Cl-Phe)-NH₂ 
• 928342-10-3 Boc-Gly-Trp-(p-Cl-Phe)-NH₂ 
• 928342-13-6 N^α-(N,N'-bis-benzyloxycarbonyl)amidino-Tyr(Me)-D-Pro-Gly-Trp-(p-Cl-Phe)-NH2 
• 1014607-97-6 C₅₂H₅₃ClN₈O₉ 
• 145232-15-1 L-(4-chloro)Phe-NH₂ 
• 1240521-25-8 (S)-tert-butyl 3-(4-chlorophenyl)-1-oxo-1-(3-(pyridin-4-yl)isoxazol-5-ylamino)propan-2-ylcarbamate 
• 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 

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.

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.

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.

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.

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.

NOVEL THIAZINE OR PYRAZINE DERIVATIVES

An object of the present invention is to synthesize novel compounds having 3-oxo-3, 4-dihydro-2H-1, 4-thiazine or 2-oxo-1, 2, 3, 4-tetrahydropyrazine as a main skeleton. The present invention relates to compounds represented by the following general formula [I] and salts thereof. In the formula, X is S or R6-(A2)n-N, R1 and R2 are H, alkyl, cycloalkyl or aryl, R3 and R4 are H, alkyl, cycloalkyl, aryl or aromatic heterocycles, R5 is H, alkyl, cycloalkyl, aryl or -A3-A4-R7, R6 is H, alkyl, cycloalkyl, OH, alkoxy, aryl, aryloxy or an aromatic heterocycle, R7 is H, alkyl, OH, alkoxy, aryl, aryloxy, amino, alkylamino, arylamino, an aromatic heterocycle or a nonaromatic heterocycle, A1 is alkylene, A2 is carbonyl or sulfonyl, A3 is alkylene, and A4 is carbonyl or oxalyl.

Process for production of optically active n-protected-n-methyl-phenylalanine derivative

There is provided a process for industrially and efficiently producing an optically active N-protected-N-methyl-4-halogenophenylalanine at a high purity, which is useful as an intermediate for the production of pharmaceutical agents. An optically active N-protected-N-methyl-4-halogenophenylalanine (including the free form and/or the salt form thereof) purified to a high purity is produced by way of the deposition and isolation in the form of salt (DCHA salt or the like) from an optically active N-protected-N-methyl-4-halogenophenylalanine containing at least the optical isomer thereof as an impurity. Because the intended compound at a high purity can be recovered and obtained at a high yield, the process of the present invention is very useful as a process for producing the intermediate for the production of pharmaceutical agents.

1-ARYL-2-ACYLAMINO-ETHANE COMPOUNDS AND THEIR USE AS NEUROKININ ESPECIALLY NEUROKININ 1 ANTAGONISTS

1-Aryl-2-acylaminoethane compounds of formula I STR1 wherein R. sub.1-R 4, X and Am are as defined in the description, have valuable pharmaceutical properties and are especially effective as NK-1 antagonists.

Aryl hydrazides as linkers for solid phase synthesis which are cleavable under mild oxidative conditions

We have developed an acid/base stable aryl hydrazide linker which is readily coupled to solid phase resins. Cleavage is specific and facile, requiring a copper (II) catalyst, base and a nucleophile to proceed. The conditions are compatible with all 20 proteinogenic amino acids and quantitative cleavage is achieved within 2 hours at 20°C to give peptides with C-terminal acid, amide or ester functionalities. Aryl hydrazides also offer scope as simple 'traceless' linkers.