Solid-phase synthesis of N,N' substituted guanidines

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5701-5704

  Dodd, Dharmpal S ^a   Wallace, Owen B ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE DERIVATIVE; N,N' BIS(T BUTOXYCARBONYL)THIOPSEUDOUREA; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ALKYLATION; ARTICLE; DRUG STRUCTURE; REACTION ANALYSIS; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032490896     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01197-6     Document Type: Article

References (16)

1. (1) Greenhill, J. V.; Lue, L. In Progress in Medicinal Chemistry, Ellis, G. P.; Luscombe, D. K. Eds.; Elsevier Science: New York, 1993; Vol. 30, Chapter 5.
2. (2) Dodd, D. S.; Kozikowski, A. P. Tetrahedron Lett. 1994, 35, 977.
3. (3) For a more thorough list of references on methods for the preparation of guanidines, see: (a) Kent, D. R.; Cody, W. L.; Doherty, A. M. Tetrahedron Lett. 1996, 37, 8711.
4. (b) Miel, H.; Rault, S. Tetrahedron Lett. 1998, 39, 1565.
5. (c) Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933.
6. (4) (a) Drewry, D. H.; Gerritz, S. W.; Linn, J. A. Tetrahedron Lett. 1997, 38, 3377.
7. (b) Kearney, P. C; Fernandez, M.; Flygare, J. A. Tetrahedron Lett. 1998,39, 2663.
8. (5) (a) Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935.
9. (b) Mitsunobu, O.; Eguchi, M. Bull. Chem. Soc. Jpn. 1971, 44, 3427. For recent reviews on C-N bond forming reactions using the Mitsunobu protocol, see
10. (c) Hughes, D. L. Org. Prep. Proc., Int. 1996, 28, 127.
11. (d) Hughes, D. L. Org. React. 1992, 42, 335.
12. (6) (a) Obrecht, D.; Abrecht, C.; Grieder, A.; Villalgordo, J. M. Helv. Chim. Acta 1997, 80, 65.
13. (b) Gayo, L. M.; Suto, M. J. Tetrahedron Lett. 1997, 38, 211.
14. 1H NMR, HPLC, LC/MS and when possible by comparison with authentic samples prepared using alternative methods.
15. 2. As an example, 5b was deprotected in quantitative yield and in >98% purity (HPLC). Some of the bis(t-butoxycarbonyl)guanidines were found to be relatively unstable to trace amount of acid or prolonged storage at rt. In some instances, partial deprotection of one of the t-Boc-groups was effected by the presence of 0.1% TFA in the preparative HPLC eluting solvent, when left at rt for a few hours.
16. 3b