Letters in Peptide Science

, Volume 10, Issue 5–6, pp 655–662 | Cite as

9-Fluorenylmethyl chloroformate (Fmoc-Cl) as a useful reagent for the synthesis of pentafluorophenyl, 2,4,5-trichlorophenyl, pentachlorophenyl, p-nitrophenyl, o-nitrophenyl and succinimidyl esters of N α-urethane protected amino acids

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Summary

9-Fluorenylmethyl chloroformate has been demonstrated to be useful reagent for the synthesis of several commonly used active esters of Fmoc-/Boc-/Z-amino acids. These include pentafluorophenyl, 2,4,5-trichlorophenyl, pentachlorophenyl, p-nitrophenyl, o-nitrophenyl, and succinimidyl esters. The method is simple, rapid and efficient. All the compounds made have been isolated as crystaline solids in good yield and optical purity. They were fully characterized by IR, and 1H NMR.

Key words

active esters 9-fluorenylmethyl chloroformate mixed anhydride racemization 

Abbreviations

Boc

t-butoxycarbonyl

DCC

dicyclohexylcarbodiimide

DCU

dicyclohexylurea;

DIEA

diisopropylethyl amine;

DMAP

4-dimethylamino pyridine

DMF

dimethylformamide

Fmoc-Cl

9-fluorenylmethyl chloroformate

SPPS

solid phase peptide synthesis

THF

tetrahydrofuran

Pfp

pentafluorophenyl

Tcp

2,4,5-trichlorophenyl

Pcp

pentachlorophenyl

ONo

o-nitrophenyl

ONp

p-nitrophenyl

ONSu

N-hydroxy succinimidyl

Z

benzyloxy carbonyl

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Copyright information

© Kluwer Academic Publishers 2004

Authors and Affiliations

  • Subramanyam J. Tantry
    • 1
  • Vommina V. Suresh Babu
    • 1
  1. 1.Department of Studies in Chemistry, Central College Campus, Dr. B. R. Ambedkar VeedhiBangalore UniversityBangaloreIndia

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