565456-75-9

Basic information

• Product Name: BOC-DL-CYCLOBUTYLALANINE
• Synonyms: BOC-DL-CYCLOBUTYLALANINE;Boc-3-Cyclobutylalanine;2-((tert-butoxycarbonyl)aMino)-3-cyclobutylpropanoic acid;N-Boc-RS-Cyclobutylalanine
• CAS NO: 565456-75-9
• Molecular Formula: C₁₂H₂₁NO₄
• Molecular Weight: 243.31
• Mol File: 565456-75-9.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: BOC-DL-CYCLOBUTYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-DL-CYCLOBUTYLALANINE(565456-75-9)
• EPA Substance Registry System: BOC-DL-CYCLOBUTYLALANINE(565456-75-9)

Safety Data

• Hazardous Substances Data: 565456-75-9(Hazardous Substances Data)

Usage

General Description

BOC-DL-CYCLOBUTYLALANINE is a chemical compound used in the synthesis and study of peptides and proteins. It is a derivative of the amino acid alanine, with a cyclobutyl group attached to the alpha carbon. The BOC (tert-butyloxycarbonyl) group is a protective group commonly used in peptide synthesis to prevent unwanted side reactions. BOC-DL-CYCLOBUTYLALANINE is used as a building block in the creation of peptides with specific structural and functional properties, and its synthesis and properties are of interest in the field of biochemistry and pharmaceutical research.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 394735-17-2 ethyl 2-amino-3-cyclobutylpropanoate 
• 816430-02-1 ethyl 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoate 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 1025799-39-6 2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester 

Downstream Products

• 394735-25-2 {(S)-2-[(1R,2S,5S)-2-(2-Carbamoyl-1-cyclobutylmethyl-2-hydroxy-ethylcarbamoyl)-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-3-yl]-1-cyclohexyl-2-oxo-ethyl}-carbamic acid tert-butyl ester 
• 394735-28-5 (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicylo[3.1.0]-hexane-2-carboxamide 
• 1036931-36-8 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride 
• 394735-22-9 tert-butyl 4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbamate 
• 394730-60-0 boceprevir 
• 394735-20-7 (2-cyano-1-cyclobutylmethyl-2-hydroxyethyl)carbamic acid tert-butyl ester 
• 394735-19-4 (2-cyclobutyl-1-formylethyl)carbamic acid tert-butyl ester 
• 394735-18-3 tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate 

Relevant articles and documents

PROCESS FOR PREPARATION OF BOCEPREVIR AND INTERMEDIATES THEREOF

THE PRESENT INVENTION RELATES TO AN IMPROVED PROCESS FOR THE PREPARATION OF (1R,5S)-N-[3-AMINO-1-(CYCLOBUTYLMETHYL)-2,3-DIOXOPROPYL]-3-[2(S)-[[[(1,1-DIMETHYLETHYL)AMINO]CARBONYL] AMINO]-3,3-DIMETHYL-1-OXOBUTYL]-6,6-DIMETHYL-3-AZABICYCLO[3.1.0]HEXAN-2(S)-CARBOXAMIDE AND ITS INTERMEDIATES

Liver/plasma concentration ratio for dosing hepatitis C virus protease inhibitor

Compositions and therapeutic combinations are provided including at least one compound selected from the group consisting of compounds of Formulae I to XXVI as defined herein as well as methods of treatment, prevention or amelioration of one or more symptoms of hepatitis C, treating disorders associated with HCV virus, modulating activity of HCV protease, in which liver to plasma concentration ratio of the compound ranges from about 2:1 to about 10:1.

Discovery of (1R,5S)-N-[3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3- [2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6, 6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a selective, potent, orally bioavailable hepatitis C virus NS3 protease inhibitor: A potential therapeutic agent for the treatment of hepatitis C infection

Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-α or polyethylene glycol (PEG)-interferon-α alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.