Home Chemistry Heterocyclic Building Blocks Oxazolidines (S)-4-Benzyloxazolidin-2-One
Nucleophilic Substitution: (S)-4-benzyloxazolidin-2-one has a carbonyl group (C=O), making it susceptible to nucleophilic substitution reactions. Nucleophiles can attack the electrophilic carbon in the carbonyl group, forming a new compound. For example, you can react it with a strong nucleophile like sodium amide to replace the oxygen with another group.
Hydrolysis: (S)-4-benzyloxazolidin-2-one can undergo hydrolysis in the presence of strong acids or bases, leading to the cleavage of the oxazolidinone ring and formation of products.
Reduction: You can reduce the carbonyl group in (S)-4-benzyloxazolidin-2-one to the corresponding alcohol using reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4).
Acylation: The carbonyl group in (S)-4-benzyloxazolidin-2-one can be acylated by reaction with acylating agents, such as acyl chlorides or anhydrides, to form new compounds.
Wittig Reaction: (S)-4-benzyloxazolidin-2-one can be used in a Wittig reaction, which is a method for the synthesis of alkenes. In this reaction, it can be reacted with a phosphonium ylide to form an alkene.
Grignard Reaction: If (S)-4-benzyloxazolidin-2-one is treated with a Grignard reagent, it can undergo a nucleophilic addition reaction to form a new compound.
Ring-opening Reactions: Depending on the reaction conditions and reagents, the oxazolidinone ring can be opened, leading to various products.
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(S)-4-Benzyl-3-propionyloxazolidin-2-one
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(S)-4-Benzyl-3-pentanoyloxazolidin-2-one
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(S)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one
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tert-Butyl (R)-4-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-methyl-4-oxobutanoate
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(S)-4-Benzyl-5,5-dimethyloxazolidin-2-one
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