Practical synthesis of an enantiomerically pure trans-4,5-disubstituted 2-pyrrolidinone via enzymatic resolution. Preparation of the LTB4 inhibitor BIRZ-227

Journal of Organic Chemistry

Volumn 63, Issue 2, 1998, Pages 326-330

  Yee, Nathan K ^a   Nummy, Laurence J ^a   Byrne, Denis P ^a   Smith, Lana L ^a   Roth, Gregory P ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 PYRIDYL) 3 (4 METHOXYPHENYL)PYRROLIDINE HEMIOXALATE; LEUKOTRIENE B4 RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; STRUCTURE ACTIVITY RELATION;

EID: 0032559310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971605p     Document Type: Article

References (26)

1. (a) Recent reviews: Musser, J. H.; Kreft, A. F. J. Med. Chem. 1992, 35, 2501.
2. (b) Summers, J. B. Drug News Perspect. 1990, 3, 3517.
3. (a) Pal, K.; Behnke, M.; Adams, J. US Patent 5594008, 1/14/97.
4. (b) Pal, K.; Behnke, M. L.; Tong, L. Tetrahedron Lett. 1993, 34, 6205.
5. For 1,3-cycloaddition chemistry of azaallyl anion see: Pearson, W. H.; Szura, D. P.; Postich, M. J. J. Am. Chem. Soc. 1992, 114, 1329.
6. Roth, G. P.; Emmanuel, M.; Tong, L. Tetrahedron Asymmetry 1997, 8, 185.
7. Yee, N. K. Tetrahedron Lett. 1997, 38, 5091 and references therein.
8. For phase transfer catalysis reactions of benzylidenebenzylamine with cinnnamic acid derivatives, see: Potapov, V. M.; Gracheva, R. A.; Sivova, N. A. Zh. Org. Khim. 1989, 25, 1876.
9. For stereoselective Michael additions of metal enolates of α-amino ester, see: (a) Tatsukawa, A.; Dan, M.; Ohbatake, M.; Kawatake, K.; Fukata, T.; Wada, E.; Kanemasa, S.; Kakei, S. J. Org. Chem. 1993, 58, 4221.
10. (b) Kanemasa, S.; Uchida, O.; Wada, E. J. Org. Chem. 1990, 55, 4411.
11. Michael adduct 6 can be isolated and characterized see ref 5.
12. The actual yield of (±)-8 was estimated to be ∼70% by flash column chromatography, see ref 5.
13. (a) Nagai, H.; Shiozawa, T.; Achiwa, K.; Terao, Y. Chem. Pharm. Bull. 1993, 41, 1933; 1992, 40, 2227.
14. (a) Nagai, H.; Shiozawa, T.; Achiwa, K.; Terao, Y. Chem. Pharm. Bull. 1993, 41, 1933; 1992, 40, 2227.
15. (b) Csomos, P.; Kanerva, L. T.; Bernath, G.; Fulop, F. Tetrahedron Asymmetry 1996, 7, 1789.
16. (c) Oumoch, S.; Rousseau, G. Bioorg. Med. Chem. Lett. 1994, 4, 2841.
17. (a) Nakano, H.; Iwasa, K.; Okuyama, Y.; Hongo, H. Tetrahedron Asymmetry 1996, 7, 2381.
18. (b) Jouglet, B.; Rousseau, G. Tetrahedron Lett. 1993, 34, 2307.
19. Patthy, A.; Vezer, C. J. Heterocycl. Chem. 1989, 26, 133.
20. Novozym 435 was purchased from Novo Nordisk Co.
21. (a) The percent ee reported in the text refers only to the trans-isomer.
22. (b) Chiral HPLC column, Daicel Chiralpak AS (4.6 mm × 25 cm); mobile phase, 25% (v/v) absolute ethanol in hexane, isocratic, 1.0 mL/min; ambient temperature. Retention times: (4S,5R)-9, 11.65 min; (4R,5S)-9, 13.09 min; (4S,5R)-10, 19.65 min; (4R,5S)-10, 24.58 min; (+)/(-)-8, 32.15 min.
23. Lipase PS-30 was purchased from Amano Co.
24. Brown, H. C.; Choi, Y. M.; Narasimhan, S. J. Org. Chem. 1982, 47, 3153.
25. HPLC column, Novapak C18 (3.9 mm × 15 cm); mobile phase, MeCN/MeOH/aqueous phosphate, pH = 2.0 (20:50:30); flow rate, 1.0 mL/min.
26. Chiral HPLC column, chiralcel OD (4.6 mm × 25 cm); mobil phase, 5% ethanol in hexane; flow rate, 1.0 mL/min; ambient temperature. Retention times: (+)-(2S,3R)-1 (BIRZ-227), 12.39 min; (-)-(2R,3S)-1, 14.05 min.