A stereospecific synthesis of both enantiomers of 2-(1'-amino-2'-methylpropyl)imidazole, a key synthon in the synthesis of SB 203386; a potent protease inhibitor

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1275-1278

  Pridgen, Lendon N ^a   Mokhallalati, Mohamed K ^a   McGuire, Michael A ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (1 AMINO 2 METHYLPROPYL)IMIDAZOLE; IMIDAZOLE DERIVATIVE; PROTEINASE INHIBITOR; SB 203386; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00070-1     Document Type: Article

References (13)

1. 1. Kohl, N. E.; Emini, E. A.; Schleif, W. A.; Davis, L. J.; Heimbach, J. C.; Dixon, R. A. F.; Scholnick, E. M.; Sigal, I. S. Proc. Natl. Acad. Sci. USA, 1988, 85, 4686.
2. 2. Abdel-Meguid, S. S.; Metcalf, B. W.; Carr, T. J.; Demarsh, P. ; DesJarlais, R. L.; Fisher, S.; Green, D. W.; Ivanoff, L.; Lambert, D. M.; Murthy, K. H. M.; Petteway, S. R.; Pitts, W. J.; Tomaszek, T. A.; Winborne, E.; Zhao, B.; Dreyer, G.; Meek, T. D. Biochemistry, 1994, 33, 11671
3. 3. Dreyer, G. B.; Lambert, D. M.; Meek, T. D.; Carr, T. J.; Tomaszek, T. A.; Fernandez, A. V.; Bartus, H.; Cacciavillani, P.; Hassell, A.; Minnich, M.; Petteway, S. R.; Metcalf, B. W.; Lewis, M. Biochemistry, 1992, 31, 6646.
4. 4. Diederich, A. M.; Ryckman, D. A. Tetrahedron Lett., 1993, 34, 6169.
5. 5. Pridgen, L. N.; Mokhallalati, M. K.; Wu, M.-J. J. Org. Chem., 1992, 57, 1237.
6. 6. Mokhallalati, M. K.; Pridgen, L. N. Synth. Commun. 1993, 23, 2055.
7. 7. For more recent examples see: (a) Miao, C. K.; Sorcek, R.; Jones, P. J. Tetrahedron Lett., 1993, 34, 2259.
8. (b) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett., 1995, 36, 7081.
9. 8. (a) Bastiaansen, L. A.; Godfroi, E. F. J. Org. Chem., 1978, 43, 1603.
10. (b) Ohta, S.; Hayakawa, S.; Nishimura, K.; Okamoto, M. Tetrahedron Lett., 1984, 25, 3251.
11. 9. Curtis, N. J.; Brown, R. S. J. Org. Chem., 1980, 45, 4038.
12. 6 and compared to an authentic sample of (S)-2.
13. 11. Mokhallalati, M. K.; Wu, M.-J.; Pridgen, L. N. Tetrahedron Lett., 1993, 34, 47.