1598387-92-8

Basic information

• Product Name: (S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate
• Synonyms: (S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate
• CAS NO: 1598387-92-8
• Molecular Weight: 430.296
• Mol File: 1598387-92-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate(1598387-92-8)
• EPA Substance Registry System: (S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate(1598387-92-8)

Safety Data

• Hazardous Substances Data: 1598387-92-8(Hazardous Substances Data)

Usage

General Description

(S)-methyl 3-(1-hydroxy-3-methylbutan-2-ylamino)-2-(5-bromo-2,4-dimethoxybenzoyl)-acrylate is a chemical compound that is composed of a methyl ester group, an amino group, and a benzoyl acrylate group. It has a molecular structure that includes a bromine atom and two methoxy groups connected to a benzene ring. This chemical compound is used in organic synthesis and pharmaceutical research due to its versatile reactivity and potential biological activity. It may have applications in the development of new drugs and materials due to its unique structure and functional groups.

Upstream product

• 2026-48-4 (S)-valinol 
• 1598387-89-3 methyl 2-(5-bromo-2,4-dimethoxybenzoyl)-3-(dimethylamino)acrylate 
• 182056-48-0 1-(5-bromo-2,4-dimethoxyphenyl)ethan-1-one 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 1598387-86-0 methyl 3-(5-bromo-2,4-dimethoxyphenyl)-3-oxopropanoate 

Downstream Products

• 697761-98-1 elvitegravir 
• 1598419-21-6 C₂₁H₃₂BrNO₆Si 

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.

A NEW PRODUCTION METHOD AND NEW INTERMEDIATES OF SYNTHESIS OF ELVITEGRAVIR

The present solution relates to an improved production method of elvitegravir of formula I, which is being clinically evaluated for treatment of HIV infection. Elvitegravir of formula I is produced via the intermediate of formula II, the preparation of which is also an object of the present solution.