4-(((((9H-fluoren-9-yl)methoxy)carbonyl)oxy)methyl)benzyl (Z)-2,2,2-trifluoro-N-phenylacetimidate

4-(((((9H-Fluoren-9-yl)methoxy)carbonyl)oxy)methyl)benzyl (Z)-2,2,2-trifluoro-N-phenylacetimidate

4-(((((9H-Fluoren-9-yl)methoxy)carbonyl)oxy)methyl)benzyl (Z)-2,2,2-trifluoro-N-phenylacetimidate is a synthetic organic compound combining an Fmoc-protected benzyl group with a trifluoroacetimidate ester. Below is its detailed structural and functional analysis:

Structural Breakdown

Core components:

1. Fmoc-protected benzyl group:
   • A 4-substituted benzyl alcohol derivative with a ((9H-fluoren-9-yl)methoxy)carbonyloxy (Fmoc-O-CO-O-) group at the para position.
   • The Fmoc group (fluorenylmethoxycarbonyl) acts as a base-labile protecting group, commonly used in peptide synthesis.
2. (Z)-2,2,2-Trifluoro-N-phenylacetimidate:
   • An imidate ester with:
     • A trifluoromethyl group (CF₃) at the α-position.
     • A phenyl group attached to the imine nitrogen.
     • (Z)-stereochemistry at the C=N bond.

Key features:

• Molecular formula: Estimated as C₃₇H₂₈F₃NO₅ (exact mass requires experimental verification).
• Functional groups:
  • Carbonate ester (linking Fmoc to benzyl).
  • Imidate ester (trifluoroacetimidate).
  • Aromatic rings (fluorenyl, benzyl, and phenyl).

Synthesis and Reactivity

• Likely synthesized via:
  1. Fmoc protection: Reaction of 4-(hydroxymethyl)benzyl alcohol with Fmoc-Cl (or Fmoc-Oxyma) to form the carbonate linkage.
  2. Imidate formation: Condensation of trifluoroacetimidic acid with the activated benzyl alcohol intermediate under acidic conditions, favoring (Z)-geometry.
• Reactivity:
  • Fmoc group removable with piperidine or DBU in DMF.
  • Imidate ester acts as a leaving group in nucleophilic substitutions or cross-couplings.

Applications

• Protecting group strategy:
  • Temporary protection of hydroxyl groups during solid-phase synthesis.
  • Orthogonal deprotection (Fmoc vs. imidate).
• Trifluoromethyl chemistry:
  • Potential use in introducing CF₃ groups into pharmaceuticals or agrochemicals.

Physicochemical Properties

• Solubility: Likely soluble in polar aprotic solvents (DMF, DCM) due to Fmoc and aromatic groups.
• Stability:
  • Sensitive to bases (Fmoc cleavage).
  • Hydrolytically unstable under acidic or aqueous conditions (imidate ester).

Safety Considerations

• Hazards:
  • Irritant (common with Fmoc derivatives).
  • Possible respiratory sensitizer (imidate esters).
• Handling: Use PPE (gloves, goggles) and work in a fume hood.

This compound exemplifies a bifunctional reagent with applications in targeted drug delivery and fluorinated molecule synthesis. Its design leverages the stability of Fmoc groups and the reactivity of trifluoroacetimidates for selective transformations.

Citations:

1. https://pubchem.ncbi.nlm.nih.gov/compound/Fmoc-4-Amb-OH
2. https://pubchem.ncbi.nlm.nih.gov/compound/Fmoc-Glu-OBzl
3. https://www.ambeed.com/products/1313054-32-8.html
4. https://pubchem.ncbi.nlm.nih.gov/compound/352523-15-0
5. https://pubchem.ncbi.nlm.nih.gov/compound/155819748
6. https://www.tcichemicals.com/assets/cms-pdfs/ReagentGuide_8th_SynthesticOrganicChemistry_MaterialsChemistry.pdf
7. https://www.pharmaffiliates.com/en/2088577-19-7-4-methylphenyl-2-o-benzoyl-3-6-di-o-benzyl-4-o-9-fluorenylmethoxycarbonyl-1-thio-beta-d-galactopyranoside-pa270026106.html
8. https://www.sigmaaldrich.com/IN/en/product/bldpharmatechcoltd/bl3h9aa4ff6d?context=bbe