N-(4-(2,5-Dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide

N-(4-(2,5-Dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide is a high-purity pharmaceutical-intermediates supplied for industrial and specialty chemical applications. Contact our team for specifications, packaging options and lead times.

1. Peptide Synthesis Intermediate

Often used as a protecting group derivative or building block in peptide and peptidomimetic synthesis.

The trifluoroacetamide unit serves as a stable protecting group for amines that can be cleaved under mild acidic or basic conditions.

2. Medicinal Chemistry & Drug Discovery

The hydantoin (oxazolidine-2,5-dione) structure is commonly found in bioactive molecules such as:

Anticonvulsants (e.g., phenytoin)

Antimicrobial agents

Antineoplastic agents

Used in the synthesis of lead-like fragments for screening and SAR (structure–activity relationship) studies.

3. Chemical Biology Research

The trifluoroacetamide group increases lipophilicity and can influence membrane permeability, making it useful in the design of prodrugs or cell-permeable compounds.

4. Stable Isotope/Fluorine-Based Probe Development

The trifluoromethyl group is useful in 19F NMR applications, enabling tracking and monitoring in fluorine-tagged molecular probes.

1. Dual Functional Scaffold

Combines two functional domains:

Trifluoroacetamide: for amine protection and improved metabolic stability.

Hydantoin core: pharmacologically relevant and chemically versatile.

2. Synthetic Flexibility

Can undergo various transformations:

N-deprotection

Nucleophilic substitutions on the hydantoin ring

Extension at the butyl chain or amidic bond

3. Enhances Bioactivity and Drug-like Properties

Trifluoromethyl substitution is known to:

Increase binding affinity

Enhance metabolic resistance

Improve pharmacokinetic profiles

4. High Stability

Chemically stable under a wide range of synthetic conditions.

Suitable for multi-step synthesis workflows in medicinal or organic chemistry labs.

N-(4-(2,5-Dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide (CAS 42267-27-6) is a versatile intermediate used in peptide synthesis, drug design, and chemical biology. Its unique structure integrates a bioactive hydantoin ring and a trifluoroacetamide group, offering advantages in synthetic accessibility, metabolic stability, and potential bioactivity. It is particularly valuable in the development of peptidomimetics, prodrugs, and fluorinated screening compounds.

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