Solid-phase synthesis of disubstituted guanidines

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2663-2666

  Kearney, Patrick C ^a   Fernandez, Monica ^a   Flygare, John A ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC AMINE; AROMATIC AMINE; GUANIDINE DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0032580389     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00373-6     Document Type: Article

References (14)

1. 1. Greenhill, J. L.; Lue, P. In Progress in Medicinal Chemistry, Ellis, G. P.; Luscombe, D. K. Eds.; Elsevier Science: New York, 1993, Vol. 30, Chapter 5.
2. 2. Bonnat, M; Bradley, M.; Kilburn, J. D. Tetrahedron Lett. 1996, 37, 5409. See footnote 11 in; Virgilio, A. A.; Schürer, S. C.; Ellman, J. A. Tetrahedron Lett. 1996, 37, 6961.
3. 2. Bonnat, M; Bradley, M.; Kilburn, J. D. Tetrahedron Lett. 1996, 37, 5409. See footnote 11 in; Virgilio, A. A.; Schürer, S. C.; Ellman, J. A. Tetrahedron Lett. 1996, 37, 6961.
4. 3. Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697. Yong, Y.F.; Kowalski, J.A.; Lipton, M.A. J. Org. Chem. 1997, 62, 1540. Kowalski, J.; Lipton, M.A. Tetrahedron Lett. 1996, 33, 5839.
5. 3. Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697. Yong, Y.F.; Kowalski, J.A.; Lipton, M.A. J. Org. Chem. 1997, 62, 1540. Kowalski, J.; Lipton, M.A. Tetrahedron Lett. 1996, 33, 5839.
6. 3. Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697. Yong, Y.F.; Kowalski, J.A.; Lipton, M.A. J. Org. Chem. 1997, 62, 1540. Kowalski, J.; Lipton, M.A. Tetrahedron Lett. 1996, 33, 5839.
7. 4. Drewry, D. H.; Gerritz, S. W.; Linn, J. A. Tetrahedron Lett. 1997, 38, 3377.
8. 5. Kearney, P. C.; Fernandez, M.; Flygare, J. A. J. Org. Chem. 1998, 63, 196.
9. 6. For references about these synthetic transformations, see: Nagarajan, S.; Ho, T. L., DuBois, G. E. Synth. Commun. 1992, 22, 1191.
10. +).
11. +).
12. 9. Purchased from Novabiochem.
13. 10. Loading levels of these resins were determined by UV spectroscopic quantitation of the dibenzofulvene product released from samples of the resin treated with 20% piperidine in DMF. See Ramage, R.; Stewart, A. J. S. J. Chem. Soc. Perkin Trans 1, 1993, 1947.
14. 6 was added to each of the samples and proton NMR spectra recorded. A 5 second delay was added between scans. The amount of guanidine present was determined by a comparison of integral peak heights of the guanidine and the reference compound. The method was tested with samples of known quantity of 2-nitrophenylacetic acid and 4-aminophenylacetic acid. For 2-nitrophenylacetic acid: determined: 0.25 mmol, actual: 0.24 mmol. For 4-aminophenylacetic acid: determined: 0.23 mmol, actual: 0.23 mmol.