Total deprotection of N,N'-bis(tert-butoxycarbonyl)guanidines using SnCl4

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7865-7866

  Miel, Hugues ^a   Rault, Sylvain ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE; GUANIDINE DERIVATIVE; STANNIC CHLORIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; SYNTHESIS;

EID: 0030778621     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10148-4     Document Type: Article

References (8)

1. Greenhill, J.L. ; Lue, P. Amidines and Guanidines in Medicinal Chemistry in "Progress in Medicinal Chemistry" Vol.30, Chapt.5, Ellis, G.P. ; Luscombe, D.K. eds. Elsevier Science, 1993
2. Yong, Y.F. ; Kowalski, J.A. ; Lipton M.A. J. Org. Chem., 1997, 62, 1540-1542 (and references therein)
3. Dodd, D.S. ; Kosikowski, A.P. Tetrahedron Lett., 1994, 35, 977-980
4. Franck, R. ; Schutkowski, M. J. Chem. Soc., Chem. Comm., 1996, 2509-2510 For a list of reagent used to cleave the Boc group, see : Greene, T.W. ; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed. ; John Wiley & Sons, New York, 1991 See also Evans, E.F. ; Lewis, N.J. ; Kapfer, I. ; Macdonald, G. and Taylor, R.J.K. Synth. Commun., 1997, 27, 1819-1825 ; Stafford, J.A., Brackeen, M.F. ; Karanewski, D.S., Valvano, N.L. Tetrahedron Lett., 1993, 34, 7873-7876
5. Franck, R. ; Schutkowski, M. J. Chem. Soc., Chem. Comm., 1996, 2509-2510 For a list of reagent used to cleave the Boc group, see : Greene, T.W. ; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed. ; John Wiley & Sons, New York, 1991 See also Evans, E.F. ; Lewis, N.J. ; Kapfer, I. ; Macdonald, G. and Taylor, R.J.K. Synth. Commun., 1997, 27, 1819-1825 ; Stafford, J.A., Brackeen, M.F. ; Karanewski, D.S., Valvano, N.L. Tetrahedron Lett., 1993, 34, 7873-7876
6. Franck, R. ; Schutkowski, M. J. Chem. Soc., Chem. Comm., 1996, 2509-2510 For a list of reagent used to cleave the Boc group, see : Greene, T.W. ; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed. ; John Wiley & Sons, New York, 1991 See also Evans, E.F. ; Lewis, N.J. ; Kapfer, I. ; Macdonald, G. and Taylor, R.J.K. Synth. Commun., 1997, 27, 1819-1825 ; Stafford, J.A., Brackeen, M.F. ; Karanewski, D.S., Valvano, N.L. Tetrahedron Lett., 1993, 34, 7873-7876
7. Franck, R. ; Schutkowski, M. J. Chem. Soc., Chem. Comm., 1996, 2509-2510 For a list of reagent used to cleave the Boc group, see : Greene, T.W. ; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed. ; John Wiley & Sons, New York, 1991 See also Evans, E.F. ; Lewis, N.J. ; Kapfer, I. ; Macdonald, G. and Taylor, R.J.K. Synth. Commun., 1997, 27, 1819-1825 ; Stafford, J.A., Brackeen, M.F. ; Karanewski, D.S., Valvano, N.L. Tetrahedron Lett., 1993, 34, 7873-7876
8. 4 are evaporated in vacuo. The remaining solid is dissolved in methanol. Ether is then added until the formation of a white precipitate of benzylguanidine hydrochloride.