816444-90-3

Basic information

• Product Name: (1R,2S,5S)-3-[(S)-2-(3-TERT-BUTYL-UREIDO)-3,3-DIMETHYL-BUTYRYL]-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID
• Synonyms: (1R,2S,5S)-3-[(S)-2-(3-TERT-BUTYL-UREIDO)-3,3-DIMETHYL-BUTYRYL]-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID;Boceprevir Metabolite M4;(1R,2S,5S)-3-[(2S)-2-[[[[1,1-DiMethylethyl]aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic Acid;(1R,2S,5S)-3-((S)-2-(3-tert-butylureido)-3,3-diMethylbutanoyl)-6,6-diMethyl-3-aza-bicyclo[3.1.0]hexane-2-carboxylic acid;3-Azabicyclo[3.1.0]hexane-2-carboxylicacid,3-[(2S)-2-[[[(1,1-diMethylethyl)aMino]carbonyl]aMino]-3,3-diMethyl-1-oxobutyl]-6,6-diMethyl-,(1R,2S,5S)-
• CAS NO: 816444-90-3
• Molecular Formula: C₁₉H₃₃N₃O₄
• Molecular Weight: 367.487
• Product Categories: Amines;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 816444-90-3.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 571.9±35.0 °C(Predicted)
• Appearance: /
• Density: 1.133
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 3.54±0.40(Predicted)
• CAS DataBase Reference: (1R,2S,5S)-3-[(S)-2-(3-TERT-BUTYL-UREIDO)-3,3-DIMETHYL-BUTYRYL]-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,5S)-3-[(S)-2-(3-TERT-BUTYL-UREIDO)-3,3-DIMETHYL-BUTYRYL]-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID(816444-90-3)
• EPA Substance Registry System: (1R,2S,5S)-3-[(S)-2-(3-TERT-BUTYL-UREIDO)-3,3-DIMETHYL-BUTYRYL]-6,6-DIMETHYL-3-AZA-BICYCLO[3.1.0]HEXANE-2-CARBOXYLIC ACID(816444-90-3)

Safety Data

• Hazardous Substances Data: 816444-90-3(Hazardous Substances Data)

Upstream product

• 1159791-82-8 3-chloro-6,6-dimethyl-3-azabicyclo[3.1.0]hexane 
• 1606175-06-7 methyl 3-((S)-2-(3-tert-butylureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate 
• 1606175-05-6 1-tert-butyl-3-((2S)-1-(2-cyano-6,6-dimethyl-3-azabicyclo[3.1.0]hexan-3-yl)-3,3-dimethyl-1-oxobutan-2-yl)urea 
• 943516-56-1 6,6-dimethyl-3-azabicyclo[3.1.0]hex-2-ene 
• 20859-02-3 L-tert-Leucine 
• 101968-85-8 (S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoic acid 
• 62965-35-9 N-tert-butyloxycarbonyl-L-tert-leucine 
• 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 
• 219753-99-8 (1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one 
• 219754-02-6 (1R,2S,5S)-3-(tert-butoxycarbonyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 
• 219754-00-4 tert-butyl (1R,2S,5S)-2-(hydroxymethyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1026427-11-1 ((1R,2S,5S)-3-Benzyl-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-2-yl)-methanol 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 

Downstream Products

• 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 
• 394730-60-0 boceprevir 
• 3651-67-0 N-methylmorpholine hydrochloride 
• 1034917-71-9 C₈H₁₇N*C₁₉H₃₃N₃O₄ 
• 877381-80-1 C₂₉H₄₃N₅O₆S 

Relevant articles and documents

SARS-COV-2 MAIN PROTEASE INHIBITORS

The present disclosure relates to certain molecules, pharmaceutical compositions containing them, and methods of using them to treat viral infections.

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

Potent inhibitors of HCV-NS3 protease derived from boronic acids

Chronic hepatitis C infection is the leading causes for cirrhosis of the liver and hepatocellular carcinoma, leading to liver failure and liver transplantation. The etiological agent, HCV virus produces a single positive strand of RNA that is processed with the help of serine protease NS3 to produce mature virus. Inhibition of NS3 protease can be potentially used to develop effective drugs for HCV infections. Numerous efforts are now underway to develop potent inhibitors of HCV protease that contain ketoamides as serine traps. Herein we report the synthesis of a series of potent inhibitors that contain a boronic acid as a serine trap. The activity of these compounds were optimized to 200 pM. X-ray structure of compound 17 bound to NS3 protease is also discussed.