[15N]-Isotopic labeling: a suitable tool to study the reactivity of bis lactams

Tetrahedron Letters

Volumn 49, Issue 5, 2008, Pages 906-909

  Coursindel, Thibault ^a   Farran, Daniel ^a   Martinez, Jean ^a   Dewynter, Georges ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

15N Isotopic labeling; Diketopiperazine; Lactam activation; Stereoselective synthesis; TRAL

Indexed keywords

2,5 DIKETOPIPERAZINE DERIVATIVE; BIS LACTAM DERIVATIVE; LACTAM DERIVATIVE; NITROGEN 15; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ISOTOPE LABELING; NITROGEN NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 37649012451     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.159     Document Type: Article

References (16)

1. Von Philipsborn W., and Müller R. Angew. Chem., Int. Ed. Engl. 25 (1986) 383-413
2. Marek R., and Lycka A. Curr. Org. Chem. 6 (2002) 35-66
3. Farran D., Parrot I., Martinez J., and Dewynter G. Angew. Chem., Int. Ed. 46 (2007) 7488-7490
4. Farran D., Toupet L., Martinez J., and Dewynter G. Org. Lett. 9 (2007) 4833-4836
5. Kanamori K., and Ross B.D. Magn. Reson. Med. 41 (1999) 456-463
6. Kanamori K., and Ross B.D. J. Magn. Reson. 139 (1999) 240-249
7. Chen J., Corbin S.P., and Holman N.J. Org. Process. Res. Dev. 9 (2005) 185-187
8. Cledera P., Avendaňo C., and Menéndez J.C. Tetrahedron 54 (1998) 12349-12360
9. López-Cobenas et al. developed a synthesis of (S)-3-isopropyl-piperazine-2,5-dione using solvent-free conditions with a domestic microwave oven operating at 600 W on the dipeptide Boc-Val-Gly-OEt for 5 min to yield 87% of the desired product. This experimental procedure cannot be used with our microwave synthetiser because we must control the temperature on our system and shows no reproducibility:. Lopez-Cobeňas A., Cledera P., Sanchez J.D., Lopez-Alvarado P., Ramos M.T., Avendaňo C., Menéndez J.C. Synthesis (2005) 3412-3422
10. Carlsson et al. reported a synthesis of (R)- and (S)-3-isopropyl-piperazine-2,5-dione using microwave irradiation (Biotage Initiater Microwave Synthetiser Producing controlled radiation at 2450 MHz and using fixed hold-time) on the dipeptide Boc-Val-Gly-OMe in water, at 150 °C for 15 min to yield 75% of the desired cyclodipeptide after recrystallization. However, this purification is quite difficult to reproduce because of the gel formation by the association of the molecules of diketopiperazines and these of the solvent or the mixture of solvents. In addition, an important degradation of the starting dipeptide is observed, due to the low stability of the methyl ester:. Carlsson A.C., Jam F., Tullberg M., Pilloti A., Ioannidis P., Luthman K., Grøtli M. Tetrahedron Lett. 47 (2006) 5199-5201
11. 2-MeOH (95:5). The organic phase is concentrated under vacuum to afford 7 as a white powder (88% yield).
12. Oba M., Terauchi T., Owari Y., Imai Y., Motoyama I., and Nishiyama K. J. Chem. Soc., Perkin Trans. 1 (1998) 1275-1281
13. sample = 15 g/L.
14. Sogn J.A., Gibbons W.A., and Randall E.W. Biochemistry 12 (1973) 2100-2105
15. Karplus S., and Karplus M. Proc. Natl. Acad. Sci. U.S.A. 69 (1972) 3204-3206
16. Atomic scattering factors were reported from International Tables for X-ray Crystallography and ORTEP views realized with platon-98. CCDC 274800 contains the supplementary crystallographic data. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk./data_request/cif.