208772-03-6

Basic information

• Product Name: ethyl 2-(N-tert-butoxycarbonyl-N-methyl)amino-3-nitrobenzoate
• Synonyms: ethyl 2-(N-tert-butoxycarbonyl-N-methyl)amino-3-nitrobenzoate
• CAS NO: 208772-03-6
• Molecular Weight: 324.334
• Mol File: 208772-03-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ethyl 2-(N-tert-butoxycarbonyl-N-methyl)amino-3-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(N-tert-butoxycarbonyl-N-methyl)amino-3-nitrobenzoate(208772-03-6)
• EPA Substance Registry System: ethyl 2-(N-tert-butoxycarbonyl-N-methyl)amino-3-nitrobenzoate(208772-03-6)

Safety Data

• Hazardous Substances Data: 208772-03-6(Hazardous Substances Data)

Upstream product

• 136285-65-9 ethyl 2-[(N-tert-butoxycarbonyl)amino]-3-nitrobenzoate 
• 74-88-4 methyl iodide 

Downstream Products

• 208772-07-0 2-(N-tert-butoxycarbonyl-N-methyl)amino-3-nitrobenzoic acid 

Relevant articles and documents

Process Development of a CRF1 Receptor Antagonist Based on the Selective Chlorination of a Benzimidazolone via Chlorine Migration

A practical synthesis of 4-chloro-2-(2,4-dichloro-6-methylphenoxy)-1-methyl-7-(pentan-3-yl)-1H-benzo[d]imidazole 1, a novel corticotropin-releasing factor 1 (CRF1) receptor antagonist, has been developed. The key chemical transformations were (1) a novel regioselective chlorination at the 4-position of a benzimidazolone intermediate with 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione in the presence of sodium tertiary butoxide via a chlorine migration mechanism (N-3 to C-4) and (2) a one-pot, three-step dehydroxylation sequence (dehydration, isomerization, and hydrogenation) of a benzylic tertiary alcohol in the presence of p-toluenesulfonic acid and a Pd catalyst. The endgame was also optimized for quality and yield improvement. The chromatography-free six-step process starting from a commercially available material afforded 1 in 35% overall yield and greater than 99% purity.