394735-20-7

Basic information

• Product Name: TERT-BUTYL 1-CYANO-3-CYCLOBUTYL-1-HYDROXYPROPAN-2-YLCARBAMATE
• Synonyms: TERT-BUTYL 1-CYANO-3-CYCLOBUTYL-1-HYDROXYPROPAN-2-YLCARBAMATE;[2-Cyano-1-(cyclobutylMethyl)-2-hydroxyethyl]-carbaMic Acid 1,1-DiMethylethyl Ester;N-[2-Cyano-1-(cyclobutylMethyl)-2-hydroxyethyl]-carbaMic Acid 1,1-DiMethylethyl Ester
• CAS NO: 394735-20-7
• Molecular Formula: C₁₃H₂₂N₂O₃
• Molecular Weight: 254.32538
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 394735-20-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 430.9°C at 760 mmHg
• Flash Point: 214.4°C
• Appearance: /
• Density: 1.115g/cm³
• Vapor Pressure: 3.12E-09mmHg at 25°C
• Refractive Index: 1.498
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• PKA: 10.77±0.20(Predicted)
• CAS DataBase Reference: TERT-BUTYL 1-CYANO-3-CYCLOBUTYL-1-HYDROXYPROPAN-2-YLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 1-CYANO-3-CYCLOBUTYL-1-HYDROXYPROPAN-2-YLCARBAMATE(394735-20-7)
• EPA Substance Registry System: TERT-BUTYL 1-CYANO-3-CYCLOBUTYL-1-HYDROXYPROPAN-2-YLCARBAMATE(394735-20-7)

Safety Data

• Hazardous Substances Data: 394735-20-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Oil

Uses

N-[2-Cyano-1-(cyclobutylMethyl)-2-hydroxyethyl]-carbaMic Acid 1,1-DiMethylethyl Ester is used in the preparation of hepatitis C virus (HCV) NS3 serine protease inhibitor.

InChI:InChI=1/C13H22N2O3/c1-13(2,3)18-12(17)15-10(11(16)8-14)7-9-5-4-6-9/h9-11,16H,4-7H2,1-3H3,(H,15,17)

Upstream product

• 394735-19-4 (2-cyclobutyl-1-formylethyl)carbamic acid tert-butyl ester 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 565456-75-9 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid 
• 394735-18-3 tert-butyl 3-cyclobutyl-1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate 
• 394735-17-2 ethyl 2-amino-3-cyclobutylpropanoate 
• 816430-02-1 ethyl 2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 17247-58-4 (Bromomethyl)cyclobutane 
• 1025799-39-6 2-(benzhydrylidene-amino)-3-cyclobutyl-propionic acid ethyl ester 

Downstream Products

• 394735-22-9 tert-butyl 4-amino-1-cyclobutyl-3-hydroxy-4-oxobutan-2-ylcarbamate 
• 394730-60-0 boceprevir 
• 1036931-36-8 3-amino-4-cyclobutyl-2-hydroxybutanamide hydrochloride 
• 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 
• 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 

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

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.

Controlled-release formulation

Controlled-release dosage formulations including at least one compound of Formulae I to XXVI herein and a controlled-release carrier and methods of treatment using the same are provided.