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

• 123795-38-0 methyl (R)-2-[(tert-butoxycarbonyl)amino]-3-(4-chlorophenyl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 14091-08-8 para-Chloro-D-phenylalanine 
• 14173-39-8 p-chlorophenylalanine 
• 7424-00-2 DL-Phe(4Cl) 
• 77-92-9 citric acid 
• 68759-85-3 para-chlorophenylalanine methyl ester 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 139377-27-8 (R)-2-Azido-3-(4-chloro-phenyl)-propionic acid 
• 35448-10-3 oxalic acid mono-tert-butyl ester 
• 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 
• 159750-02-4 (4S,2S)-4-Chloro-<2-azido-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 

Downstream Products

• 475094-99-6 [1-(4-chlorobenzyl)-2-(4-cyclohexyl-4-[1,2,4]triazole-1-ylmethyl-piperidin-1-yl)-2-oxo-ethyl]carbamic acid tert-butyl ester 
• 475095-06-8 {1-(4-chloro-benzyl)-2-[4-cyclohexyl-4-(1H-tetrazol-5-ylmethyl)-piperidin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 475095-00-2 [1-(4-chloro-benzyl)-2-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 766550-02-1 N-(tert-butoxycarbonyl)-4-chloro-D-phenylalanine 4-nitrobenzyl ester 
• 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 

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.

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.