1598387-97-3

Basic information

• Product Name: (R)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate
• Synonyms: (R)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate
• CAS NO: 1598387-97-3
• Molecular Weight: 430.296
• Mol File: 1598387-97-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate(1598387-97-3)
• EPA Substance Registry System: (R)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)acrylate(1598387-97-3)

Safety Data

• Hazardous Substances Data: 1598387-97-3(Hazardous Substances Data)

Upstream product

• 1598387-86-0 methyl 3-(5-bromo-2,4-dimethoxyphenyl)-3-oxopropanoate 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 182056-48-0 1-(5-bromo-2,4-dimethoxyphenyl)ethan-1-one 
• 4276-09-9 (R)-2-amino-3-methylbutanol 
• 1598387-89-3 methyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-(dimethylamino)acrylate 

Downstream Products

• 1177256-05-1 6-(3-chloro-2-fluorobenzyl)-1-((2R)-1-hydroxy-3-methylbutan-2-yl)-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 

Relevant articles and documents

An Improved Synthesis of Elvitegravir

An improved process for the active pharmaceutical ingredient of a new HIV integrase inhibitor elvitegravir (1) has been developed. It starts from commercially available 2,4-dimethoxyacetophenone, which is selectively halogenated into the position 5. The 5-halo acetophenones are condensed with dialkyl carbonates to give the corresponding benzoylacetates. Their treatment with N,N-dimethylformamide dimethyl acetal followed by (S)-valinol then provided the corresponding intermediate benzoyl acrylates. Cyclization to the required 1,4-dihydroquinolin-4-oxo derivatives by aromatic nucleophilic substitution of the 2-methoxy group was achieved by treatment with N,O-bis(trimethylsilyl)-acetamide, which also protected the OH group as the trimethylsilyl derivative. Finally, the Negishi coupling with 2-fluoro-3-chlorobenzylzinc bromide and the following hydrolysis provided elvitegravir (1). The preferred variant, the seven-step procedure starting from 2,4-dimethoxyacetophenone, provides elvitegravir in 29.3% yield.