Poly(ethylene glycol) as solvent and polymer support in the microwave assisted parallel synthesis of aminoacid derivatives
10.1016/s0040-4039(00)01067-4
Crossref journal-article
Elsevier BV
Tetrahedron Letters (78)
Bibliography

Sauvagnat, B., Lamaty, F., Lazaro, R., & Martinez, J. (2000). Poly(ethylene glycol) as solvent and polymer support in the microwave assisted parallel synthesis of aminoacid derivatives. Tetrahedron Letters, 41(33), 6371–6375.

Authors 4
  1. Bérengère Sauvagnat (first)
  2. Frédéric Lamaty (additional)
  3. René Lazaro (additional)
  4. Jean Martinez (additional)
References 24 Referenced 46
  1. (a) Caddick, S. Tetrahedron 1995, 51, 10403–10432. (10.1016/0040-4020(95)00662-R)
  2. (b) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathé, D. Synthesis 1998, 1213–1234. (10.1055/s-1998-6083)
  3. Deshayes, S.; Liagre, M.; Loupy, A.; Luche, J.-L.; Petit, A. Tetrahedron 1999, 55, 10851–10870. (10.1016/S0040-4020(99)00601-8)
  4. (a) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. Tetrahedron Lett. 1998, 39, 821–824. (10.1016/S0040-4039(97)10722-5)
  5. (b) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. J. Comb. Chem. 2000, 2, 134–142. (10.1021/cc9900605)
  6. (a) Sauvagnat, B.; Lamaty, F.; Lazaro, R.; Martinez, J. C. R. Acad. Paris Série IIc 1998, 1, 777–780.
  7. (b) Nouvet, A.; Binard, M.; Lamaty, F.; Martinez, J.; Lazaro, R. Tetrahedron 1999, 55, 4685–4698. (10.1016/S0040-4020(99)00130-1)
  8. (c) Bouifraden, S.; Drouot, C.; El Hadrami, M.; Guenoun, F.; Lecointe, L.; Mai, N.; Paris, M.; Pothion, C.; Sadoune, M.; Sauvagnat, B.; Amblard, M.; Aubagnac, J. L.; Calmes, M.; Chevallet, P.; Daunis, J.; Enjalbal, C.; Fehrentz, J. A.; Lamaty, F.; Lavergne, J. P.; Lazaro, R.; Rolland, V.; Roumestant, M. L.; Viallefont, P.; Vidal, Y.; Martinez, J. Amino Acids 1999, 16, 345–379. (10.1007/BF01388176)
  9. For a review, see: (a) Totten, G. E.; Clinton, N. A. J. M. S. Rev. Macromol. Chem. Phys. 1988, C28, 293–337. (10.1080/15583728808085378)
  10. (b) Totten, G. E.; Clinton, N. A.; Matlock, P. L. J. M. S. Rev. Macromol. Chem. Phys. 1998, C38, 77–142. (10.1080/15583729808545778)
  11. For selected examples: (a) Berdagué, P.; Perez, F.; Courtieu, J.; Bayle, J. P. Bull. Soc. Chim. Fr. 1993, 130, 475–480. (b) Abribat, B.; Le Bigot, Y.; Gaset, A. Synth. Comm. 1994, 24, 1773–1779. (c) Abribat, B.; Le Bigot, Y.; Gaset, A. Synth. Comm. 1994, 24, 2091–2096. (d) Abribat, B.; Le Bigot, Y. Tetrahedron 1997, 53, 2119–2124. For an example involving a PEG 6000, see: Neumann, R.; Sasson, Y. Tetrahedron 1983, 39, 3437–3440. (10.1016/S0040-4020(01)91597-2)
  12. For an example of PEG supported synthesis using microwave with water as solvent see: Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. J. Org. Chem. 1999, 64, 3885–3890. (10.1021/jo982135h)
  13. For an example of microwave mediated esterification on a soluble poly(styrene-co-allylalcohol)polymer: Vanden Eynde, J.-J.; Rutot, D. Tetrahedron 1999, 55, 2687–2694. (10.1016/S0040-4020(99)00051-4)
  14. Microwave activated alkylation of a benzaldehyde Schiff base glycine has been described: Jiang, Y.; Wang, Y.; Deng, R.; Mi, A. In Phase Transfer Catalysis, Mechanisms and Syntheses; Halpern, M. E., Ed.; ACS Symposium Series 659:Washington DC, 1996; p. 203.
  15. Microwave-assisted reactions were performed in an open pyrex glass vessel (beaker, 2 cm diameter, 2 mm thick glass) with a Brandt MS 1100 Domestic Microwave oven at a frequency of 2450 Hz and a power of 850 W. Caution: the inorganic base must be well distributed by previous mixing with the organic compounds in order to avoid the destruction of the reaction vessel. A representation procedure for the synthesis of 4e is as follows: Cinnamyl bromide (11.8 mg, 0.06 mmol) was added to poly(ethylene glycol) 3400 N-(diphenylmethylene) glycinate (80 mg, 0.02 mmol) and Cs2CO3 (39 mg, 0.12 mmol). The mixture was heated under microwave for 45 min. After cooling, the product was dissolved in CH2Cl2, then filtered. The filtrate was concentrated, dissolved in CH2Cl2, filtered, and then precipitated in Et2O. The product was filtered and dried in vacuo to yield 80 mg (98%) of the title compound: IR (KBr) 2865 (m), 1736 (s), 1655 (s), 1459 (s), 1100 (m), 954 (m) cm−1; 1H NMR (CDCl3, Me4Si) δ 2.70–2.90 (m, 2H), 3.50–3.80 (s large, 310H), 4.05–4.15 (m, 1H), 4.20–4.30 (m, 2H), 5.90–6.15 (m, 1H), 6.30–6.45 (d, J=15.5 Hz, 1H), 7.10–7.40 (m, 13H), 7.55–7.70 (m, 2H); 13C NMR (CDCl3, Me4Si) δ 37.48, 64.44, 65.78, 69.36, 126.40, 127.49, 128.27, 128.40, 128.83, 128.86, 129.03, 129.18, 130.73, 133.08, 136.72, 137.68, 139.85, 171.17, 171.99.
  16. All new compounds have been characterized by IR, 1H NMR, 13C NMR and ESI mass spectrometry.
  17. Blettner, C. G.; König, W. A.; Stenzel, W.; Schotten, T. Synlett 1998, 295–297. (10.1055/s-1998-1630)
  18. Conventional alkylation of Schiff base protected glycine in the solid-phase has been described: (a) O'Donnell, M. J.; Zhou, C.; Scott, W. L. J. Am. Chem. Soc. 1996, 118, 6070–6071. (b) O'Donnell, M. J.; Lugar, C. W.; Pottorf, R. S.; Zhou, C. Tetrahedron Lett. 1997, 38, 7163–7166. (c) Domı́nguez, E.; O'Donnell, M. J.; Scott, W. L. Tetrahedron Lett. 1998, 39, 2167–2170. (d) O'Donnell, M. J.; Delgado, F.; Pottorf, R. S. Tetrahedron 1999, 55, 6347–6362. (10.1021/ja9601245)
  19. (a) Larhed, M.; Lindeberg, G.; Hallberg, A. Tetrahedron Lett. 1996, 37, 8219–8222. (10.1016/0040-4039(96)01872-2)
  20. (b) Chen, S. T.; Tseng, P. H.; Yu, H. M.; Wu, C. Y.; Hsiao, K. F.; Wu, S. H.; Wang, K. T. J. Chin. Chem. Soc. 1997, 44, 169–182. (10.1002/jccs.199700028)
  21. (c) Hsieh, H. P.; Chen, S. T.; Wang, K. T. J. Chin. Chem. Soc. 1997, 44, 597–600. (10.1002/jccs.199700092)
  22. (d) Yu, A. M.; Zhang, Z. P.; Yang, H. Z.; Zhang, C. X.; Liu, Z. Synth. Commun. 1999, 29, 1595–1599. (10.1080/00397919908086140)
  23. (e) Hoel, A. M. L.; Nielsen, J. Tetrahedron Lett. 1999, 40, 3941–3944. (10.1016/S0040-4039(99)00616-4)
  24. (f) Chandrasekhar, S.; Padmaja, M. B.; Raza, A. Synlett 1999, 1597–1599. (10.1055/s-1999-2894)
Dates
Type When
Created 23 years, 1 month ago (July 25, 2002, 6:03 a.m.)
Deposited 5 years, 7 months ago (Jan. 7, 2020, 8:19 p.m.)
Indexed 1 year, 8 months ago (Jan. 2, 2024, 7:19 a.m.)
Issued 25 years, 1 month ago (Aug. 1, 2000)
Published 25 years, 1 month ago (Aug. 1, 2000)
Published Print 25 years, 1 month ago (Aug. 1, 2000)
Funders 0

None

@article{Sauvagnat_2000, title={Poly(ethylene glycol) as solvent and polymer support in the microwave assisted parallel synthesis of aminoacid derivatives}, volume={41}, ISSN={0040-4039}, url={http://dx.doi.org/10.1016/s0040-4039(00)01067-4}, DOI={10.1016/s0040-4039(00)01067-4}, number={33}, journal={Tetrahedron Letters}, publisher={Elsevier BV}, author={Sauvagnat, Bérengère and Lamaty, Frédéric and Lazaro, René and Martinez, Jean}, year={2000}, month=aug, pages={6371–6375} }