Novel method for the loading of nucleophiles on multipin crowns

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5477-5480

  Tommasi, Ruben A ^a   Nantermet, Philippe G ^a   Shapiro, Michael J ^b   Chin, Jefferson ^b   Brill, Wolfgang K D ^a   Ang, Kiah ^c  

^a NOVARTIS PHARMA AG   (Switzerland)

^b CTA Novartis Pharmaceut Corporation   (United States)

^c Migenix Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; COVALENT BOND; DRUG DESIGN; METHODOLOGY; REACTION ANALYSIS;

EID: 0032581663     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01137-X     Document Type: Article

References (9)

1. 1. Nestler, H.P.; Bartlett, P.A. and Still, W.C. J. Org. Chem. 1994, 59, 4723-4724. Nefzi, A., Ostresh, J.M. and Houghten, R.A. Chem. Rev. 1997a, 97, 449-472.
2. 1. Nestler, H.P.; Bartlett, P.A. and Still, W.C. J. Org. Chem. 1994, 59, 4723-4724. Nefzi, A., Ostresh, J.M. and Houghten, R.A. Chem. Rev. 1997a, 97, 449-472.
3. 2. Bray, A.M.; Chiefari, D.S.; Valerie, R.M. and Maeji, N.J. Tetrahedron Lett. 1995, 36, 5081-5084.
4. 3. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
5. 4. Related cations and radicals are known to be stable and in fact, commercially available. Such examples are the galvinoxyl radical available from Aldrich and also the cation illustrated below, (dimethoxy-(trimethoxybenzylidene)-cyclohexa-dienylidene)-methyl oxonium chloride, which is available from Salor. (formula presented)
6. 2 for 1 hour. Products were isolated by evaporation of the cleavage solution and drying in vacuo to constant weight.
7. 6. Crowns with the FMOC Rink amide linker were obtained from Chiron Technologies, Australia.
8. 7. The yields reported for the amines are for the respective TFA salts. Potassium carbonate was added to improve the reactivity of the carboxyl group by deprotonation. This resulted in only a modest improvement in the yield although the red color of the cation disappears within a few minutes
9. 8. Chin, J.; Fell, B.; Shapiro, M.J.; Tomesh, J.; Wareing, J.R. and Bray, A.M. J. Org. Chem. 1997, 62, 538-539.