Description

(2R,4R)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (CAS No. 681128-51-8) is a high-purity fluorinated proline derivative designed for advanced research and pharmaceutical applications. This compound features a tert-butoxycarbonyl (Boc) protecting group and a fluorine substituent at the 4-position of the pyrrolidine ring, offering exceptional stereochemical control for peptide synthesis and medicinal chemistry. With a molecular formula of C₁₀H₁₆FNO₄, it serves as a critical chiral building block for the development of protease inhibitors, enzyme substrates, and bioactive molecules. Available in >98% HPLC purity, this reagent is supplied as a white to off-white crystalline powder, ensuring optimal performance in asymmetric synthesis and structure-activity relationship (SAR) studies. Store under inert conditions at -20°C for long-term stability.

Properties

• CAS Number: 681128-51-8
• Complexity: 300
• IUPAC Name: (2R,4R)-1-tert-butoxycarbonyl-4-fluoro-pyrrolidine-2-carboxylic acid
• InChI: InChI=1S/C10H16FNO4/c1-10(2,3)16-9(15)12-5-6(11)4-7(12)8(13)14/h6-7H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m1/s1
• InChI Key: YGWZXQOYEBWUTH-RNFRBKRXSA-N
• Exact Mass: 233.10633615
• Molecular Formula: C10H16FNO4
• Molecular Weight: 233.24
• SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@@H]1C(=O)O)F
• Topological: 66.8
• Monoisotopic Mass: 233.10633615
• Synonyms: 681128-51-8, (2R,4R)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid, (2R,4R)-1-[(tert-butoxy)carbonyl]-4-fluoropyrrolidine-2-carboxylic acid, (2R,4R)-1-Boc-4-fluoropyrrolidine-2-carboxylic acid, (4R)-1-Boc-4-fluoro-D-proline, (2R,4R)-4-fluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid, MFCD02684479, (2R,4R)-1-Boc-4-fluoro-2-pyrrolidinecarboxylic Acid, C10H16FNO4, Boc-D-cis-Pro(4-F)-OH, SCHEMBL2489604, GCB12851, AKOS024258735, HY-W061614, AS-52788, DS-018135, CS-0053468, P15646, EN300-1589836, (2R,4R)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylicacid, Boc-cis-D-Pro(4-F)-OH; (2R,4R)-1-(tert-Butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic Acid, N-t-Butoxycarbonyl-cis-4-fluoro-D-proline;(2R,4R)-1-t-Butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid

This fluorinated Boc-protected proline derivative is widely utilized in peptide synthesis to introduce conformational constraints and enhance metabolic stability. It serves as a key intermediate in the preparation of fluorinated peptidomimetics and protease inhibitors targeting serine/threonine proteases. Researchers employ it in solid-phase peptide synthesis (SPPS) and structure-based drug design due to its ability to modulate backbone torsion angles. The fluorine atom’s strong electronegativity makes it valuable for ¹⁹F NMR studies of protein-ligand interactions.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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