Fluorenylmethyloxycarbonyl chloride

Fluorenylmethyloxycarbonyl chloride[1]
Ball-and-stick model of the fluorenylmethyloxycarbonyl chloride molecule
Names
IUPAC name
Chloroformic acid 9H-fluoren-9-ylmethyl ester
Other names
9-Fluorenylmethyl chloroformate; 9-Fluorenylmethoxycarbonyl chloride; Fmoc-chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.816
Properties
C15H11ClO2
Molar mass 258.70 g·mol−1
Melting point 62 to 64 °C (144 to 147 °F; 335 to 337 K)
Hazards
Corrosive (C)
R-phrases (outdated) R34
S-phrases (outdated) S26 S36/37/39 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Fluorenylmethyloxycarbonyl chloride (FMOC-Cl) is a chloroformate ester. It is used to introduce FMOC group as the FMOC carbamate.

Preparation

This compound may be prepared by reacting 9-fluorenylmethanol with phosgene:[2]

Reactions

The FMOC carbamate is often used as a protecting group for amines. The FMOC group can be introduced by reacting the amine with FMOC-Cl, e.g.:[3]

The other common method for introducing the FMOC group is through 9-fluorenylmethylsuccinimidyl carbonate (FMOC-OSu), which may itself be obtained by the reaction of FMOC-Cl with the dicyclohexylammonium salt of N-hydroxysuccinimide.[4]

It may be cleaved by bases, typically a solution of piperidine:

FMOC protection has found significant use in solid phase peptide synthesis because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin.[5]

Because the fluorenyl group is highly fluorescent, certain UV-inactive compounds may be reacted to give the FMOC derivatives, suitable for analysis by reversed phase HPLC. Analytical uses of FMOC-Cl that do not use chromatography may be limited by the requirement that excess FMOC-Cl be removed before an analysis of fluorescence.

Amine Protection - Fluorenylmethyloxycarbonyl (Fmoc)

Fluorenylmethyloxycarbonyl (Fmoc) group is used as a protecting group for amines in organic synthesis.

Common amine protection methods

Common amine deprotection methods


References

  1. Fmoc chloride at Sigma-Aldrich
  2. Carpino, Louis A.; Han, Grace Y. (1972). "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry. 37 (22): 3404. doi:10.1021/jo00795a005.
  3. Yamada, Kazuhiko; Hashizume, Daisuke; Shimizu, Tadashi; Ohki, Shinobu; Yokoyama, Shigeyuki (2008). "A solid-state 17O NMR, X-ray, and quantum chemical study of N-α-Fmoc-protected amino acids". Journal of Molecular Structure. 888: 187. doi:10.1016/j.molstruc.2007.11.059.
  4. Paquet, A. (1982). "Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates". Canadian Journal of Chemistry. 60 (8): 976. doi:10.1139/v82-146.
  5. J. Jones, Amino Acid and Peptide Synthesis, 2nd edn., Oxford University Press, 2002.
  6. Carpino, Louis A.; Han, Grace Y. "9-Fluorenylmethoxycarbonyl amino-protecting group". The Journal of Organic Chemistry. 37 (22): 3404–3409. doi:10.1021/jo00795a005.
  7. Wuts, P; Green, T (2006); "Greene's Protective Groups in Organic Synthesis"; DOI: 10.1002/9780470053485.
  8. Farrera-Sinfreu, Josep; Royo, Miriam; Albericio, Fernando (2002-10-21). "Undesired removal of the Fmoc group by the free ε-amino function of a lysine residue". Tetrahedron Letters. 43 (43): 7813–7815. doi:10.1016/S0040-4039(02)01605-2.
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