Determination of the enantiomeric purity and the configuration of β- aminoalcohols using (R)-2-fluorophenylacetic acid (AFPA) and fluorine-19 NMR: Application to β-blockers

Tetrahedron Asymmetry

Volumn 11, Issue 14, 2000, Pages 2885-2898

  Apparu, Marcel ^a   Ben Tiba, Younes ^a   Léo, Pierre Marc ^a   Hamman, Sylvain ^a   Coulombeau, Christian ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINOALCOHOL; ATENOLOL; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; ESTER; METOPROLOL; OXPRENOLOL; PHENYLACETIC ACID DERIVATIVE; PINDOLOL; PRACTOLOL; PROPRANOLOL;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DIASTEREOISOMER; DRUG DETERMINATION; DRUG PURITY; ENANTIOMER; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 0343664417     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00254-8     Document Type: Article

References (40)

1. Parker, D. Chem. Rev. 1991, 91, 1441-1457.
2. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
3. Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
4. Latypov, S. K.; Seco, J. M.; Quinoa, E.; Riguera, R. J. Org. Chem. 1996, 61, 8569-8577, and references cited therein.
5. Latypov, S. K.; Seco, J. M.; Quinoa, E.; Riguera, R. J. Org. Chem. 1995, 60, 1538-1545, and references cited therein.
6. Trost, B. M.; Bunt, R. C.; Pulley, S. R. J. Org. Chem. 1994, 59, 4202-4205.
7. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
8. Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
9. Hoye, T. R.; Renner, M. K. J. Org. Chem. 1996, 61, 8489-8495.
10. Ohtani, I.; Kusumi T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096, and references cited therein.
11. Kusumi, T.; Fukushima, T.; Ohtani, I.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2939-2942.
12. 13-15
13. Parker, D. J. Chem. Soc., Perkin Trans. 2 1983, 83-88.
14. Heumann, A.; Faure, F. J. Org. Chem. 1993, 55, 1276-1279, and references cited therein.
15. Fukushi, Y.; Yajima, S.; Mizutani, J. Tetrahedron Lett. 1994, 599-602.
16. Maddaluno, J.; Corruble, A.; Leroux, V.; Ple, G.; Duhamel, P. Tetrahedron: Asymmetry 1992, 3, 1239-1242.
17. Brown, H. C.; Salunkhe, A. M.; Singaram, B. J. Org. Chem. 1991, 56, 1170-1175.
18. Joshi, B. S.; Newton, M. G.; Lee, D. W.; Barber, A. D.; Pelletier, S. W. Tetrahedron: Asymmetry 1996, 7, 25-28.
19. Khan, M. A.; Tavares, D. F.; Rauk, A. Can. J. Chem. 1982, 60, 2451-2455.
20. Hamman, S.; Barrelle, M.; Tetaz, F.; Beguin, C. G. J. Fluorine Chem. 1987, 37, 85-93.
21. Barrelle, M.; Hamman, S. J. Chem. Res. 1990 (S), 100-101, 1990 (M), 701-709.
22. Barrelle, M.; Hamman, S. J. Chem. Res. 1990 (S), 100-101, 1990 (M), 701-709.
23. Apparu, M.; Ben Tiba, Y.; Léo, P. M.; Mathieu, J. P.; Mauclaire, L. J. Labelled Cpd. Radiopharm. 1999, 42, 1195-1202.
24. Apparu, M.; Demenge, P.; Fagret, D.; Ghezzi, C.; Majid, S.; Mathieu, J. P.; Mauclaire, L.; Pasqualini, R.; Vidal, M. International Pat. WO96/00717; Chem. Abstr. 1996, 124, 288981v.
25. Apparu, M.; Demenge, P.; Fagret, D.; Ghezzi, C.; Majid, S.; Mathieu, J. P.; Mauclaire, L.; Pasqualini, R.; Vidal, M. International Pat. WO96/00717; Chem. Abstr. 1996, 124, 288981v.
26. Apparu, M.; Ben Tiba, Y.; Léo, P. M.; Dao Boulanger, T. H.; Mauclaire, L.; Mathieu, J. P.; Carbonnelle, E.; Fagret, D. 4th International Conference on Nuclear and Radiochemistry, St Malo, Sept. 8-13, 1996.
27. 2) is completely absent from the NMR spectrum of 11. On the other hand, the two doublets of the only AB system present are perfectly separated between 3.51 and 3.75 ppm.
28. Ben Tiba, Y. Thesis, Université Joseph Fournier, Grenoble, 1997.
29. Imperial Chemical Industries Ltd., British Patent 1,078,852, 1968; Chem. Abstr. 1966, 65, 7099f.
30. Crowther, A. F.; Howe, R.; Smith, L. H. J. Med. Chem. 1971, 14, 511-513.
31. Danilewicz, J. C.; Kemp, E. G. J. Med. Chem. 1973, 16, 168-169.
32. Korn, N.; Gibson, J. K.; Kniffen, F. J.; Lucchesi, B. R.; Ranade, V. V.; Mimnaugh, M.; Yu, T.; Counsell, R. E. J. Pharm. Sci. 1980, 69, 1010-1013.
33. Nelson, W. L.; Burke Jr., T. R. J. Org. Chem. 1978, 43, 3641-3645.
34. Belgian Patent 669402; Chem. Abstr. 1966, 65, 5402d.
35. Laskina, E. D.; Devitskaya, T. A.; Belov, V. N. Tr. Vses. Nauchn. Issled. Inst. Sintetich i Natural'n. Dushistykh Veshchestv. 1963, 6, 31-37; Chem. Abstr. 1964, 61, 11919b.
36. Laskina, E. D.; Devitskaya, T. A.; Belov, V. N. Tr. Vses. Nauchn. Issled. Inst. Sintetich i Natural'n. Dushistykh Veshchestv. 1963, 6, 31-37; Chem. Abstr. 1964, 61, 11919b.
37. Bäckvall, J. E.; Byström, S. E. J. Org. Chem. 1982, 47, 1126-1128.
38. Shtacher, G.; Rubinstein, R.; Somani, P. J. Med. Chem. 1978, 21, 678-683.
39. Kunz, W.; Jacobi, H.; Koch, K. German Patent 1967, 1236523; Chem. Abstr. 1967, 66, 64046k.
40. Kunz, W.; Jacobi, H.; Koch, K. German Patent 1967, 1236523; Chem. Abstr. 1967, 66, 64046k.