(2R,4S)-4-Fluoropyrrolidine-2-carboxylic acid, CAS No. 131176-02-8

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131176-02-8

Catalog No. EBD43085

CAS 131176-02-8

Name (2R,4S)-4-Fluoropyrrolidine-2-carboxylic acid

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Basic Information

Synonyms: (2R,4S)-4-Fluoropyrrolidine-2-carboxylicacid (2R,4S)-4-Fluoro-2-pyrrolidinecarboxylicacid (4S)-4-Fluor-D-prolin (4S)-4-Fluoro-D-proline D-proline,4-fluoro-,(4S)- (2R,4S)-4-fluoropyrrolidinium-2-carboxylate trans-4-fluoro-d-proline (2r,4s)-4-fluoro-2-proline

Molecular Formula: C5H8FNO2

Molecular Weight: 133.12

MDL Number: MFCD07366527

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

(2R,4S)-4-Fluoropyrrolidine-2-carboxylic acid is a non-proteinogenic amino acid derivative featuring a fluorinated pyrrolidine ring. This chiral compound, with defined stereochemistry at the 2- and 4-positions, serves as a crucial building block in medicinal chemistry. Its primary application is as a key intermediate in the synthesis of pharmaceutical agents, particularly protease inhibitors. The fluorinated pyrrolidine scaffold is a privileged structure that mimics natural amino acids, enhancing metabolic stability and binding affinity. It has been extensively utilized in the research and development of drugs targeting diseases such as hepatitis C and COVID-19, where it functions as a component of peptidomimetic inhibitors. The introduction of fluorine alters the electronic and steric properties of the molecule, influencing its pKa, lipophilicity, and conformation. This makes it a valuable tool for structure-activity relationship (SAR) studies in drug discovery programs focused on modulating biological targets like viral proteases.

Physical Properties

Boiling Point: 265.1°Cat760mmHg

Flash Point: 114.1°C

Density: 1.3g/cm3