N-BOC-cis-4-fluoro-L-proline, CAS No. 203866-13-1

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203866-13-1

Catalog No. EBD7411

CAS 203866-13-1

Name N-BOC-cis-4-fluoro-L-proline

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Basic Information

Synonyms: (2S,4S)-4-Fluoro-N-Boc-Pyrrolidine-2-carboxylicacid N-t-BOC-cis-4-Fluoro-L-proline Boc-cis-4-fluoro-Pro-OH (2S,4S)-Boc-4-fluoro-pyrrolidine-2-carboxylicacid (2S,4S)-4-Fluoro-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylicacid N-BOC-cis-4-fluoro-L-proline (4S)-1-(tert-butoxycarbonyl)-4-fluoro-L-proline Boc-cis-4-F-L-Pro-OH

Molecular Formula: C10H16FNO4

Molecular Weight: 233.24

MDL Number: MFCD04973957

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

N-Boc-cis-4-fluoro-L-proline is a fluorinated, Boc-protected derivative of the non-proteinogenic amino acid cis-4-fluoro-L-proline. It serves as a crucial chiral building block in medicinal chemistry and peptide research. The introduction of fluorine at the 4-position of the proline ring significantly alters the ring's conformational preference (pucker), which can enhance the metabolic stability, bioavailability, and binding affinity of peptide-based drug candidates. Its primary application is as a key intermediate in the synthesis of novel therapeutic peptides and peptidomimetics. The cis-fluoro substitution is particularly valuable for engineering peptides with improved pharmacological profiles, making it a sought-after reagent in the development of protease inhibitors, receptor agonists/antagonists, and other bioactive molecules targeting various diseases. It is a specialty chemical with high value in pharmaceutical R&D. As a protected amino acid derivative, it is also a fundamental organic synthesis building block, specifically categorized as an amine and a heterocyclic compound. It is typically handled under standard laboratory conditions for air- and moisture-sensitive reagents.

Physical Properties

Melting Point: 157-161 °C (D)

Boiling Point: 346 °C at 760 mmHg

Flash Point: 163 °C

Density: 1.24 g/cm3

Refractivity: -57 ° (C=1, MeOH)