A new method for the synthesis of carboxamides and peptides using 1,1′-carbonyldioxydi[2(1H)-pyridone] (CDOP) in the absence of basic promoters

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1951-1955

  Shiina, Isamu ^a   Kawakita, Yo Ichi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' CARBONYLDIOXYDI[2(1H) PYRIDONE]; 4 DIMETHYLAMINOPYRIDINE; AMIDE; AMINE; AMINO ACID DERIVATIVE; BENZYLOXYCARBONYLGLYCYLPHENYLALANYLVALYLMETHYL OXIDE; BENZYLOXYCARBONYLPHENYLALANYLVALYLALANYLMETHYL OXIDE; CARBOXYLIC ACID DERIVATIVE; OXIDE; PEPTIDE DERIVATIVE; PYRIDONE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0037463474     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00063-7     Document Type: Article

References (40)

1. Benz G. Trost B.M., Fleming I. Comprehensive Organic Synthesis. 6:1991;381-417 Pergamon, Oxford.
2. (CDI): Staab H.A., Lüking M., Dürr F.H. Chem. Ber. 95:1962;1275-1283 (DPPA): Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205; Takuma, S.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull. 1982, 30, 3147-3153.
3. (DEPC): Yamada S., Kasai Y., Shioiri T. Tetrahedron Lett. 14:1973;1595-1598.
4. (BOP): Castro B., Dormoy J.R., Evin G., Selve C. Tetrahedron Lett. 16:1975;1219-1222.
5. (HBTU, TBTU): Knorr R., Trzeciak A., Bannwarth W., Gillessen D. Tetrahedron Lett. 30:1989;1927-1930.
6. (HATU): Carpino L.A. J. Am. Chem. Soc. 115:1993;4397-4398.
7. (o-hydroxybenzenesulfonyl chloride): Cabaret D., Wakselman M. Tetrahedron Lett. 35:1994;9561-9564.
8. (BOMI, BDMP, BPMP, DOMP, SOMP, FOMP, AOMP): Li P., Xu J.-C. Tetrahedron. 56:2000;4437-4445.
9. (BEP, FEP, BEPH, FEPH): Li P., Xu J.-C. Tetrahedron. 56:2000;8119-9131.
10. (CMBI): Li P., Xu J.-C. Tetrahedron. 56:2000;9949-9955.
11. (HOTT, TOTT, HODT, TODT): Albericio F., Bailén M.A., Chinchilla R., Dodsworth D.J., Nájera C. Tetrahedron. 57:2001;9607-9613.
12. Williams M.W., Young G.T. J. Chem. Soc. 1964;3701-3708.
13. Williams A. J. Chem. Soc., Perkin 2. 1975;947-953.
14. Curran T.C., Farrar C.R., Niazy O., Williams A. J. Am. Chem. Soc. 102:1980;6828-6837.
15. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. 1999;503-504 John Wiley & Sons, New York.
16. Shiina I., Suenaga Y., Nakano M., Mukaiyama T. Bull. Chem. Soc. Jpn. 73:2000;2811-2818.
17. Shiina, I.; Saitoh, K.; Nakano, M.; Suenaga, Y.; Mukaiyama, T. Collect. Czech. Chem. Commun. 2000, 65, 621-630.
18. See also: (b) Shiina, I.; Saitoh, K.; Fréchard-Ortuno, I.; Mukaiyama, T. Chem. Lett. 1998, 3-4; (c) Saitoh, K.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1998, 679-680; (d) Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem. Eur. J. 1999, 5, 121-161.
19. See also: (b) Shiina, I.; Saitoh, K.; Fréchard-Ortuno, I.; Mukaiyama, T. Chem. Lett. 1998, 3-4; (c) Saitoh, K.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1998, 679-680; (d) Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem. Eur. J. 1999, 5, 121-161.
20. See also: (b) Shiina, I.; Saitoh, K.; Fréchard-Ortuno, I.; Mukaiyama, T. Chem. Lett. 1998, 3-4; (c) Saitoh, K.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1998, 679-680; (d) Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem. Eur. J. 1999, 5, 121-161.
21. Shiina, I.; Saitoh, K.; Nakano, M.; Suenaga, Y.; Mukaiyama, T. Collect. Czech. Chem. Commun. 2000, 65, 621-630. See also: (b) Shiina, I.; Saitoh, K.; Fréchard-Ortuno, I.; Mukaiyama, T. Chem. Lett. 1998, 3-4; (c) Saitoh, K.; Shiina, I.; Mukaiyama, T. Chem. Lett. 1998, 679-680; (d) Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem. Eur. J. 1999, 5, 121-161.
22. CDOP was synthesized as follows. To a mixture of 2-hydroxypyridine N-oxide (1.00 g, 9.00 mmol) and triphosgene (450 mg, 1.51 mmol) in dichloromethane (30 mL) at 0°C under an argon atmosphere was added pyridine (1.5 mL). After the reaction mixture had been stirred for 24 h at room temperature, the solvent was evaporated. The residue was washed with ether three times (each 30 mL) under an argon atmosphere. The crude CDOP was dissolved in THF (50 mL) and the suspension including pyridine·HCl salt was stirred for 2 h at room temperature and then it was allowed to stand for 30 min. After filtration of the mixture under an argon atmosphere and evaporation of the solvent at 45°C, THF (50 mL) was added to the yellow residue, and then the above operation was repeated three times. Dichloromethane (each 3 mL) and ether (each 6 mL) were successively added to the resulted mixture and the yellow solution was separated from white precipitates under an argon atmosphere, and then the above operation was repeated twice. The remaining solvent was removed under reduced pressure at 45°C to produce CDOP (1.02 g, 91%) as a white solid.
23. 3): δ 156.3 (2), 150.2 (C=O), 140.0 (4), 134.5 (6), 122.9 (3), 105.5 (5).
24. 3): δ 162.9 (2), 139.7 (6), 138.8 (4), 120.2 (3), 105.8 (5), 37.4 (Me).
25. 2): δ 7.81-5.32 (9H, m, Ph, Py), 3.11-3.06 (2H, m, H-3), 2.99-2.93 (2H, m, H-2).
26. (a) Miyashita, M.; Shiina, I.; Miyoshi, S.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1993, 66, 1516-1527 and references cited therein.
27. See also: (b) Shoda, S.; Mukaiyama, T. Chem. Lett. 1980, 391-392.
28. (a) Miyashita, M.; Shiina, I.; Miyoshi, S.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1993, 66, 1516-1527 and references cited therein. See also: (b) Shoda, S.; Mukaiyama, T. Chem. Lett. 1980, 391-392.
29. Van der Auwera C., Van Damme S., Anteunis M.J.O. Int. J. Pept. Protein Res. 29:1987;464-471.
30. Carpino L.A., El-Faham A., Albericio F. J. Org. Chem. 60:1995;3561-3564.
31. R=13.8 min (D form).
32. R=10.6 min (DL form).
33. R=17.9 min (LDL form).
34. Fujino M., Hatanaka C. Chem. Pharm. Bull. 16:1968;929-932.
35. Heslinga L., Arens J.F. Recl. Trav. Chim. Pays-Bas. 76:1957;982-995.
36. Young R.W., Wood K.H., Joyce R.J., Anderson G.W. J. Am. Chem. Soc. 78:1956;2126-2131.
37. Jones J.H., Young G.T. J. Chem. Soc. (C). 1968;53-61.
38. Mukaiyama T., Matsueda R., Suzuki M. Tetrahedron Lett. 11:1970;1901-1904.
39. Pedersen U., Thorsen M., El-Khrisy E.-E.A.M., Clausen K., Lawesson S.-O. Tetrahedron. 38:1982;3267-3269.
40. Yamada T., Kurokawa S., Dejima K., Watanabe K., Kotani M., Miyazawa T., Kuwata S. Mem. Konan Univ., Sci. Ser. 32:1985;11-26.