The Synthetic Routes of dl-norepinephrine-4-O-sulfate

dl-Norepinephrine-4-O-sulfate, also known as N-[2-[[4-(dibutylamino)-2-oxo-1,3-oxazolidin-3-yl]amino]ethyl]-N'-[4-[[4-(dibutylamino)-2-oxo-1,3-oxazolidin-3-yl]amino]butyl]-2-oxo-1,3-oxazolidine-3-sulfate, is a synthetic chemical compound that is commonly used in the chemical industry.
It is a derivative of norepinephrine, a naturally occurring neurotransmitter that plays a crucial role in the regulation of blood pressure, heart rate, and other physiological processes.

The synthesis of dl-norepinephrine-4-O-sulfate involves a multi-step synthesis route that involves a combination of chemical reactions such as substitution, condensation, and oxidation.
The synthesis route can be broadly classified into two categories: classical and modern synthesis routes.

Classical Synthesis Route
The classical synthesis route of dl-norepinephrine-4-O-sulfate involves several steps, including the preparation of the starting materials and the use of hazardous reagents such as hydrogen sulfide and fuming nitric acid.
The steps involved in the classical synthesis route are as follows:

1. Preparation of 2-oxo-1,3-oxazolidine-3-one: This compound is prepared by treating 1,3-oxazolidine-3-one with hydrogen peroxide in the presence of a mineral acid catalyst such as sulfuric acid.
   
2. O-Sulfation of 2-oxo-1,3-oxazolidine-3-one: This step involves the treatment of 2-oxo-1,3-oxazolidine-3-one with sulfuric acid to form the sulfate ester.
   
3. Preparation of dibutylamine: This compound is prepared by treating butanamine with dibromoethane in the presence of a solvent such as ether.
   
4. Preparation of N-[2-[[4-(dibutylamino)-2-oxo-1,3-oxazolidin-3-yl]amino]ethyl]-N'-[4-[[4-(dibutylamino)-2-oxo-1,3-oxazolidin-3-yl]amino]butyl]-2-oxo-1,3-oxazolidine-3-sulfate: This compound is prepared by treating 2-oxo-1,3-oxazolidine-3-one and dibutylamine with a condensation agent such as dicyclohexylcarbodiimide (DCC) in the presence of a solvent such as dichloromethane.
   

Modern Synthesis Route
The modern synthesis route of dl-norepinephrine-4-O-sulfate uses more efficient and environmentally friendly reagents and procedures compared to the classical synthesis route.
The steps involved in the modern synthesis route are as follows:

1. Preparation of 2-oxo-1,3-oxazolidine-3-one: This compound is prepared by treating 1,3-oxazolidine-3-one with hydrogen peroxide in the presence of a transition metal catalyst such as palladium on barium sulfate.
   
2. O-Sulfation of 2-oxo-1,3-oxazolidine-3-one: This step involves the treatment of 2-oxo-1,3-oxazolidine-3-one with sulfuric acid in the presence of a solvent such as toluene.
   
3. Preparation of dibutylamine: This compound is prepared by treating butanamine with dibromoethane in the presence of a solvent such as tetrahydrofuran.
   
4. Preparation of N-[2-[[4-(dibutylamino)-2-oxo-1,3-oxazolidin-3-yl]amino]ethyl]-N'-[4-[[4-(dibutylamino)-2-oxo-1,3-oxazolidin-3-