873055-54-0

Basic information

• Product Name: Carbonic acid, 2,4-bis(1,1-diMethylethyl)phenyl Methyl ester
• Synonyms: Carbonic acid, 2,4-bis(1,1-diMethylethyl)phenyl Methyl ester;(2,4-ditert-butylphenyl) Methyl carbonate;2,4-bis(1,1-diMethylethyl)phenyl Methyl ester;carbonic acid 2,4-di-tert-butylphenyl ester methyl ester;Carbonic acid mono-(2,4-di-tert-butyl-phenyl) ester
• CAS NO: 873055-54-0
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.35996
• Mol File: 873055-54-0.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbonic acid, 2,4-bis(1,1-diMethylethyl)phenyl Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic acid, 2,4-bis(1,1-diMethylethyl)phenyl Methyl ester(873055-54-0)
• EPA Substance Registry System: Carbonic acid, 2,4-bis(1,1-diMethylethyl)phenyl Methyl ester(873055-54-0)

Safety Data

• Hazardous Substances Data: 873055-54-0(Hazardous Substances Data)

Usage

Uses

Carbonic acid, 2,4-bis(1,1-diMethylethyl)phenyl Methyl Ester is used in the synthesis of triazoles as amide biosteres in cystic fibrosis transmembrane conductance regulator modulators.

Upstream product

• 96-76-4 2,4-di-tert-Butylphenol 
• 79-22-1 methyl chloroformate 

Downstream Products

• 873055-55-1 carbonic acid 2,4-di(tert-butyl)-5-nitrophenyl ester methyl ester 
• 873055-56-2 carbonic acid 2,4-di(tert-butyl)-6-nitrophenyl ester methyl ester 
• 1236058-25-5 N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-6-(trifluoromethyl)-1,4-dihydroquinoline-3-carboxamide 
• 873051-19-5 N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide 
• 1236058-06-2 N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxamide 
• 1236060-10-8 N-(2,4-di-tert-butyl-5-hydroxyphenyl)-6-methyl-4-oxo-1,4-dihydroquinoline-3-carboxamide 
• 1643-39-6 2-amino-4,6-di-tertbutylphenol 
• 873055-58-4 5-amino-2-4-di-tert-butyl-phenol 
• 873055-57-3 2,4-di-tert-butyl-5-nitro-phenol 
• 1246213-45-5 2,4-di-tert-butyl-5-(4-oxo-1,4-dihydroquinoline-3-carboxamido)phenyl methyl carbonate 
• 873054-44-5 ivacaftor 
• 1182822-31-6 5-amino-2,4-di-tert-butylphenyl methyl carbonate 
• 20039-94-5 2,4-di-tert-butyl-6-nitrophenol 

Relevant articles and documents

COMPOUND FOR TREATING CYSTIC FIBROSIS

Provided herein is a compound represented by Formula I: or a pharmaceutically acceptable salt, hydrate, solvate or complex thereof. Also provided are pharmaceutical compositions comprising the compound noted above, in combination with a pharmaceutically acceptable excipient.

METHODS OF TREATMENT FOR CYSTIC FIBROSIS

This application describes methods of treating cystic fibrosis or a CFTR mediated disease comprising administering Compound I or a pharmaceutically acceptable salt thereof. (I) The application also describes pharmaceutical compositions comprising Compound I or a pharmaceutically acceptable salt thereof and optionally comprising one or more additional CFTR modulating agents.

Utilizing o-Quinone Methide Chemistry: Synthesis of d9-Ivacaftor

Lead time and cost are important factors for any pharmaceutical API. However, these issues become even more important when the drug substance contains an isotope such as deuterium, which has a natural abundance of only ～0.016% of all hydrogen. Fewer suppliers and logistical barriers both play a role in driving up the cost. These factors can challenge the supply route used to manufacture d9-ivacaftor (17), requiring investigation into alternative routes. By adapting the work from Pettus et al., a synthetic approach utilizing a transient o-quinone methide allowed access to the deuterium-labeled o-tert-butylphenol moiety. This was developed and proven on pilot scale to significantly reduce the number of deuterated reagents used, leading to an overall reduction in cost by a factor of 10, while also providing the substantial benefit of applying prior process knowledge from the parent, nonisotopically enriched API ivacaftor (7).