In certain clinical situations, there is need for an injectable B-blocker with a short biological half-life. The clue to development of such a drug was taken from the struc- ture of atenolol, whose corresponding carboxylic acid (the product of hydrolysis of its amide) has no B-blocking activity. Substituting an ester for the amide group and lengthening the carbon side chain by one methylene group resulted in esmolol. Its ester group is hydrolyzed quite rapidly to a carboxyl group by serum esterases under physiological conditions. This hydrolysis product has no B-blocking activity. OMe + CI HO NH2 4-Hydroxycinnamic acid Esmolol Isopropyl- amine Epichloro- hydrin
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
Is esmolol chiral? If so, which of the possible stereoisomers are formed in this synthesis?
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