133261-17-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide is used as a potential pharmaceutical agent for its structural features that may allow for specific interactions with biological targets, potentially leading to novel therapeutic applications.
Used in Biological Research:
In the field of biological research, (R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide may serve as a valuable compound for studying the interactions between small molecules and biological systems, contributing to the understanding of molecular mechanisms and the development of new drugs.

Upstream product

• 94-71-3 2-Ethoxyphenol 
• 112101-81-2 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide 

Downstream Products

• 106133-20-4 tamsulosin hydrochloride 
• 133261-19-5 tamsulosin hydrochloride 
• 106133-20-4 (R)-tamsulosin 

Relevant academic research and scientific papers

A PROCESS FOR THE PREPARATION OF R (-) TAMSULOSIN HYDROCHLORIDE

The invention discloses a process for the preparation of highly pure R (-)-5-(2-(2-(2-ethoxy phenoxy) ethylamine) propyl)-2-methoxy benzene sulfonamide hydrochloride used to treat symptoms of urinary difficulty. R-(-)-2-(4-methoxy phenyl)- 1 -methyl ethyl amine is condensed with halo-acetyl halide in the presence of base and a halogenated solvent. The resulting R-(-)- halo-N-[2-(4-methoxy phenyl)- 1 -methyl ethyl] acetamide is treated with chlorosulphonic acid and ammonia. R-(-)-N-[2-(3-amino sulfonyl-4-methoxy phenyl)- 1 -methyl ethyl]-2- haloacetamide obtained is treated with 2- ethoxy phenol in the presence of an inorganic base and water to obtain R-(-)-N-[2-(3-amino sulfonyl-4-methoxy phenyl)- 1 -methyl ethyl]-2-(2- ethoxy phenoxy) acetamide in high yield and purity. The amide obtained is reduced to obtain the Tamsulosin base, which is then purified and converted to its hydrochloride salt.

METHOD OF PREPARING OPTICALLY PURE PHENETHYLAMINE DERIVATIVES

Provided is a method of preparing an optically pure compound having formula 1 or its salts. The method includes: reacting -2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methylethylamine or its salts with a compound selected form the group consisting of chloroacetic acid, bromoacetic acid, fluoroacetic acid, iodoacetic acid, α-halogenoacetic acid anhydride, and α-halogenoacetyl halide in the presence of a base or an acylating agent.

PROCESS FOR THE PREPARATION OF TAMSULOSIN

There is provided a process for the preparation of tamsulosin of formula 5, involving a coupling reaction in the presence of an aluminum reagent between an ester of formula 2A and (R)-5-(2-amino)propyl-2-methoxy-benzenesulfonamide of formula 3 to yield tamsulosin amide, which is then reduced to yield tamsulosin.