201848-57-9

Basic information

• Product Name: 3-[(2-bromo-2-methyl-propionyl)-isopropyl-amino]-4-hydroxy-benzoic acid methyl ester
• Synonyms: 3-[(2-bromo-2-methyl-propionyl)-isopropyl-amino]-4-hydroxy-benzoic acid methyl ester
• CAS NO: 201848-57-9
• Molecular Weight: 358.232
• Mol File: 201848-57-9.mol

Chemical Properties

• CAS DataBase Reference: 3-[(2-bromo-2-methyl-propionyl)-isopropyl-amino]-4-hydroxy-benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[(2-bromo-2-methyl-propionyl)-isopropyl-amino]-4-hydroxy-benzoic acid methyl ester(201848-57-9)
• EPA Substance Registry System: 3-[(2-bromo-2-methyl-propionyl)-isopropyl-amino]-4-hydroxy-benzoic acid methyl ester(201848-57-9)

Safety Data

• Hazardous Substances Data: 201848-57-9(Hazardous Substances Data)

Upstream product

• 201848-59-1 4-(2-bromo-2-methyl-propionyloxy)-3-isopropylamino-benzoic acid methyl ester 
• 536-25-4 methyl 3-amino-4-hydroxybenzoate 
• 201848-58-0 methyl 4-hydroxy-3-isopropylaminobenzoate 

Relevant articles and documents

An acid-catalyzed O,N-acyl migration and application to the synthesis of N-(4-isopropyl-2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6- carbonyl) guanidine methanesulfonate (KB-R9032), a novel Na/H exchange inhibitor

In the search for a practical synthesis of N-(4-isopropyl-2,2-dimethyl- 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl)guanidine methanesulfonate (KB-R9032), a potent Na/H exchange inhibitor, the acylation of methyl 4- hydroxy-3-isopropylaminobenzoate 6a with 2-bromoisobutyryl bromide was carried out in order to prepare an N-acyl derivative, 8a. However, an O-acyl derivative 7a was obtained selectively. Acylations of derivatives of 6a were examined. The results revealed that the O-acylation occurred because of the steric repulsion between the N-isopropyl moiety and the bulky acyl bromide. Then, we investigated the O,N-acyl migration of 7a. We found that the migration was catalyzed by carboxylic acid and that 8a was precipitated from a diisopropyl ether solution in good yield. Treatment of 8a with potassium carbonate and subsequent guanidine gave the synthetic intermediate for KB- R9032 in high yield.