219754-02-6

Basic information

• Product Name: Boceprevir interMediate
• Synonyms: Boceprevir interMediate;(1R,2S,5S)-3-(tert-butoxycarbonyl)-6,6-diMethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid;Racemic-(1R,2S,5S)-3-(Tert- Butoxycarbonyl)-6,6-Dimethyl-3- Azabicyclo[3.1.0]Hexane-2- Carboxylic Acid;Racemic-(1R,2S,5S)-3-(Tert-Butoxycarbonyl)-6,6-Dimethyl-3-Azabicyclo[3.1.0]Hexane-2-Carboxylic Acid(WX112069)
• CAS NO: 219754-02-6
• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.31014
• Mol File: 219754-02-6.mol

Chemical Properties

• Boiling Point: 361.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.179±0.06 g/cm3(Predicted)
• PKA: 4.04±0.40(Predicted)
• CAS DataBase Reference: Boceprevir interMediate(CAS DataBase Reference)
• NIST Chemistry Reference: Boceprevir interMediate(219754-02-6)
• EPA Substance Registry System: Boceprevir interMediate(219754-02-6)

Safety Data

• Hazardous Substances Data: 219754-02-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boceprevir intermediate is used as a key intermediate in the synthesis of boceprevir, an antiviral medication for the treatment of chronic hepatitis C virus (HCV) infection. It plays a crucial role in the manufacturing process, undergoing chemical reactions and modifications to form the final boceprevir compound.
Boceprevir intermediate is used as a building block for the production of boceprevir, a protease inhibitor that inhibits the replication of the HCV virus. This helps to improve liver function in HCV-infected individuals and contributes to addressing the global burden of HCV infection.

Upstream product

• 219754-00-4 tert-butyl (1R,2S,5S)-2-(hydroxymethyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 134107-65-6 (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 
• 103201-79-2 (3R,7aS)-3-phenyl-tetrahydro-pyrrolo[1,2-c]oxazol-5-one 
• 1026427-11-1 ((1R,2S,5S)-3-Benzyl-6,6-dimethyl-3-aza-bicyclo[3.1.0]hex-2-yl)-methanol 
• 219753-99-8 (1S,2S,4S,7R)-6-aza-3,3-dimethyl-8-oxa-7-phenyltricyclo<4.3.0.0>nonan-5-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 394734-84-0 (1R,2S,5S)-(6,6-dimethyl-3-azabicyclo[3.1.0]hex-2-yl)methanol 
• 569679-06-7 3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 
• 911835-76-2 (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 

Downstream Products

• 219754-03-7 (1R,2S,5S)-6,6-Dimethyl-3-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-benzyl ester 3-tert-butyl ester 
• 569679-06-7 3-(tert-butyl) 2-methyl (1R,2S,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 
• 219754-08-2 Piv-PTL-PTL-OBn 

Relevant articles and documents

ANTIVIRAL COMPOUNDS FOR THE TREATMENT OF CORONAVIRUS, PICORNAVIRUS AND NOROVIRUS INFECTIONS

Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating coronavirus, Picomavirus and Norovims infections with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.

A facile and efficient synthesis of 3,3-dimethyl isopropylidene proline from (+)-3-carene

(Chemical Equation Presented) A highly efficient and practical route to 3,4-isopropylidene proline I, starting from (+)-3-carene, was developed. The three continuous stereocenters were constructed using the inherent chirality of the starting natural product 2. The overall yield for the 12-step synthesis is 34%. The optimized sequence leading to 1 has been successfully applied on a multigram scale, thereby establishing the practicality of this route.

HCV PROTEASE INHIBITORS AND USES THEREOF

The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

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.