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Synthesis 2008(23): 3739-3741  
DOI: 10.1055/s-0028-1083227
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

tert-Butoxycarbonyl Chloride for the Introduction of N-Boc Groups into Amino Acids

Helmut Vorbrüggen*a,b
a (The Former) Woodward Research Institute, 4000 Basel, Switzerland
b Institut für Chemie und Biochemie, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany
e-Mail: helvor@chemie.fu-berlin.de;
Further Information

Publication History

Received 7 July 2008
Publication Date:
14 November 2008 (online)

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Abstract

tert-Butoxycarbonyl chloride (BocCl) can be generated in situ from tert-butyl alcohol, COCl2, and pyridine at -74 ˚C to introduce the Boc group in high yield into a hindered amino acid. The method is suitable for large-scale preparations of Boc-amino acids.

Key words

Boc chloride - COCl2 - pyridine - mixed anhydrides - amino acids

    References

  • 1 Woodward RB. Heusler K. Gosteli J. Naegeli P. Oppolzer W. Ramage R. Ranganathan S. Vorbrüggen H. J. Am. Chem. Soc.  1966,  88:  852 
    CrossrefSearch in Google Scholar
  • 2 Woodward GE. Schroeder EF. J. Am. Chem. Soc.  1937,  59:  16903 
    Search in Google Scholar
  • 3 Kemp DS. Carey RI. J. Org. Chem.  1989,  54:  3640 
    CrossrefSearch in Google Scholar
  • 4 Okamura K. Nakamura Y. Shin C.-G. Bull. Chem. Soc. Jpn.  1999,  72:  1561 
    CrossrefSearch in Google Scholar
  • 5 Shiraiwa T. Kataoka K. Sakata S. Kurokawa H. Bull. Chem. Soc. Jpn.  1988,  61:  4158 
    CrossrefSearch in Google Scholar
  • 6 Wuts PGM. Greene TW. Protective Groups in Organic Chemistry   4th ed.:  Wiley; New York: 2006. 
    Search in Google Scholar
  • 7 Kozienski PJ. Protecting Groups   3rd ed.:  Thieme Verlag; Stuttgart: 2004.  p.59-61  
    Search in Google Scholar
  • 8 Kreher R. Bockhorn GH. Angew. Chem., Int. Ed. Engl.  1964,  3:  589 
    Search in Google Scholar
  • 9 Howe JH. Morris LR. J. Org. Chem.  1962,  27:  1901 
    CrossrefSearch in Google Scholar
  • 10 Nikisch K. Klose W. Bohlmann F. Chem. Ber.  1980,  113:  2036 
    CrossrefSearch in Google Scholar
  • 11 Grehn L. Ragnarsson U. Angew. Chem., Int. Ed. Engl.  1984,  23:  291 
    Search in Google Scholar
  • 12 Grehn L. Ragnarsson U. Angew. Chem., Int. Ed. Engl.  1985,  24:  510 
    CrossrefSearch in Google Scholar
  • 13 Steglich W. Höfle G. Vorbrüggen H. Angew. Chem., Int. Ed. Engl.  1978,  17:  569 
    CrossrefSearch in Google Scholar
  • 14 Cook AH. Heilbron IM. In The Chemistry of Penicillin   Princeton University Press; Princeton NJ: 1949.  p.958 
  • 15 Chopin A. Rogers J. J. Am. Chem. Soc.  1948,  70:  2967 
    CrossrefSearch in Google Scholar
  • 16 Pozdnev VF. Tetrahedron Lett.  1993,  36:  7115 
    Search in Google Scholar
  • 17 Pozdnev VF. Org. Prep. Proced. Int.  1998,  30:  631 
    CrossrefSearch in Google Scholar
  • 18 Nicolaou KC. Nevalainen M. Safina BS. Zak M. Bulat B. Angew. Chem. Int. Ed.  2002,  41:  1942 
    Search in Google Scholar
  • 19 Okamura K. Nakamura Y. Shin C.-G. Umemura K. Yoshimura J. Bull. Chem. Soc. Jpn.  1998,  71:  1863 
    CrossrefSearch in Google Scholar
  • 20 Miyoshi M, and Onishi T. inventors; Japanese Patent JP  46000011.  ; Chem. Abstr. 1971, 74, 111596
  • 21 Miyazaki S, Soeda Y, and Kiyama M. inventors; Japanese Patent  JP 10114715.  ; Chem. Abstr. 1998, 128, 308228
  • 22 Miyoshi M, and Onoshi T. inventors; Japanese Patent  JP 45035533.  ; Chem. Abstr. 1970, 74, 124866
  • 23 Sakakibara S, and Honda I. inventors; German Patent  DE 2108782.  ; Chem. Abstr. 1971, 76, 24715
  • 24 Yamashita K, Watanabe Y, and Sumi A. inventors; Japanese Patent  JP 49075531.  ; Chem. Abstr. 1974, 82, 97684
  • 25 Losse G, Klengel H, Riechert R, and Schumacher J. inventors; German Patent  DD 106166.  ; Chem. Abstr. 1974, 81,152633
  • 26 Sato T, Furukawa H, and Nagasaki F. inventors; Japanese Patent  JP 2001302556.  ; Chem. Abstr. 2001, 135, 318504
  • 27 Christensen BG, and Leanza WJ. inventors; US Patent  US 3780031.  ; Chem. Abstr. 1974, 80, 108549
  • 28 Watkins KJ. Chem. Eng. News  2001,  (January 8):  11 
    Search in Google Scholar