N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

Synlett

Volumn , Issue 2, 2000, Pages 189-192

  Suzuki, Masumi ^a   Yamazaki, Takahiro ^a   Ohta, Hiromichi ^a   Shima, Kyoko ^a   Ohi, Katsuhide ^a   Nishiyama, Shigeru ^a   Sugai, Takeshi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

Enzymes; Hydrolysis; N carbamylamino alcohols; N nitrosourea; Oxazolidinones

Indexed keywords

AMINOALCOHOL; NITROUS ACID; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DEAMINATION; DERIVATIZATION; DRUG SYNTHESIS; HYDROLYSIS; NITROSATION; REACTION ANALYSIS; SOLUBILITY;

EID: 0033978397     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6508     Document Type: Article

References (67)

1. (a) Brickner, S. J. Curr. Pharm. Design 1996, 2, 175-194.
2. (b) Close, W. J. J. Am. Chem. Soc. 1951, 73, 95-98.
3. c) Gleave, D. M.; Brickner, S. J. J. Org. Chem. 1996, 61, 6470-6474.
4. d) Tucker, J. A.; Allwine, D. A.; Grega, K. C.; Barbachyn, M. R.; Klock, J. L.; Adamski, J. L.; Brickner, S. J.; Hutchinson, D. K.; Ford, C. W.; Zurenko, G. E.; Conradi, R. A.; Burton, P. S.; Jensen, R. M. J. Med. Chem. 1998, 41, 3727-3735.
5. (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
6. (b) Kunieda, T.; Ishizuka, T. Yukigosei Kagaku Kyokaishi (J. Synth. Org. Chem. Jpn.) 1997, 55, 1018-1028.
7. (a) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417.
8. (b) Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
9. (c) Smith, A. B., III; Kozmin, S. A.; Paone, D. V. J. Am. Chem. Soc. 1999, 121, 7423-7424.
10. (d) Gerlach, K.; Quitschalle, M.; Kalesse, M. Tetrahedron Lett. 1999, 40, 3553-3556.
11. (e) Mapp, A. K.; Heathcock, C. H. J. Org. Chem. 1999, 64, 23-27.
12. (f) Williams, D. R.; Clark, M. P.; Berliner, M. A. Tetrahedron Lett. 1999, 40, 2287-2290.
13. (g) Pearson, C.; Rinehart, K. L.; Sugano, M. Tetrahedron Lett. 1999, 40, 411-414.
14. (h) Matsushima, T.; Zheng, B.-Z.; Maeda, H.; Nakajima, N.; Uenishi, J.; Yonemitsu, O. Synlett 1999, 780-782.
15. i) Haigh, D.; Birrell, H. C.; Cantello, B. C. C.; Eggleston, D. S.; Haltiwanger, R. C.; Hindley, R. M.; Ramaswamy, A.; Stevens, N. C. Tetrahedron: Asymmetry 1999, 10, 1353-1367.
16. (j) White, J. D.; Carter, R. G.; Sundermann, K. F. J. Org. Chem. 1999, 64, 684-685.
17. (k) Bigot, A.; Tran Huu Dau, M. E.; Zhu, J. J. Org. Chem. 1999, 64, 6283-6296.
18. Bänteli, R.; Brun, I.; Hall, P.; Metternich, R. Tetrahedron Lett. 1999, 40, 2109-2112.
19. (a) Hintermann, T.; Seebach, D. Helv. Chim. Acta 1998, 81, 2093-2126.
20. (b) Tomoyasu, T.; Tomooka, K.; Nakai, T. Synlett 1998, 1147-1149.
21. c) Sibi, M. P.; Ji, J.; Sausker, J. B.; Jasperse, C. P. J. Am. Chem. Soc. 1999, 121, 7517-7526.
22. (a) Matsunaga, H.; Ishizuka, T.; Kunieda, T. Tetrahedron 1997, 53, 1275-1294.
23. (b) Rück-Braun, K.; Stamm, A.; Engel, S.; Kunz, H. J. Org. Chem. 1997, 62, 967-975.
24. (a) Wuts, P. G. M.; Pruitt, L. E. Synthesis 1989, 622-623.
25. (b) Gage, J. R.; Evans, D. A. Org. Synth. 1989, 68, 77-82.
26. (c) Sibi, M. P.; Renhowe, P. A. Tetrahedron Lett. 1990, 31, 7407-.7410.
27. (d) Maleski, R. J.; Osborne, C. E.; Cline, S. M. J. Heterocyclic Chem. 1991, 28, 1937-1939.
28. (e) Knölker, H.-J.; Braxmeier, T. Tetrahedron Lett. 1998, 39, 9407-9410.
29. (a) Pridgen, L. N.; Prol, J., Jr.; Alexander, B.; Gillyard, L. J. Org. Chem. 1989, 54, 3231-3233.
30. (b) Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Akiba, T.; Terashima, S. Tetrahedron Lett. 1992, 33, 3487-3490.
31. (c) O'Hagan, D.; Tavasli, M. Tetrahedron: Asymmetry 1999, 10, 1189-1192.
32. (a) Eckert, H.; Forster, B. Angew. Chem. Int. Ed. Engl. 1987, 26, 894-895.
33. (b) Sicker, D. Synthesis 1989, 875-876.
34. c) Gibson, C. L.; Gillon, K.; Cook, S. Tetrahedron Lett. 1998, 39, 6733-6736.
35. Kubota, Y.; Kodaka, M.; Tomohiro, T.; Okuno, H. J. Chem. Soc., Perkin Trans. 1 1993, 5-6.
36. (a) Ishimaru, T. Nippon Kagaku Zasshi 1960, 81, 1428-1431.
37. (b) Ishimaru, T. Nippon Kagaku Zasshi 1960, 81, 1589-1592.
38. (c) Nachman, R. J. J. Heterocydic Chem. 1983, 20, 1423-1425.
39. (a) Snyder, J. K.; Stock, L. M. J. Org. Chem. 1980, 45, 886-891.
40. (b) Collet, H.; Bied, C.; Mion, L.; Taillades, J.; Commeyras, A. Tetrahedron Lett. 1996, 37, 9043-9046.
41. Taillades, J.; Collet, H.; Garrel, L.; Beuzelin, I.; Boiteau, L.; Choukroun, H.; Commeyras, A. J. Mol. Evol. 1999, 48, 638-645.
42. Newman, M. S.; Kutner, A. J. Am. Chem. Soc. 1951, 73, 4199-4204.
43. (a) Itsuno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K. J. Chem. Soc., Perkin Trans. 1 1985, 2039-2044.
44. (b) Davies, S. G.; Sanganee, H. J. Tetrahedron: Asymmetry 1995, 6, 671-674.
45. -1. The spectral data of 1a-1e and 9 were identical with those of commercially available samples.
46. Delaunay, D.; Toupet, L.; Le Corre, M. J. Org. Chem. 1995, 60, 6604-6607.
47. (a) Ibuka,T.; Chu, G.-N.; Aoyagi, T.; Kitada, K.; Tsukida, T.; Yoneda, F. Chem. Pharm. Bull. 1985, 33, 451-453.
48. (b) Knölker, H.-J.; Braxmeier, T.; Schlechtingen, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 2497-2500.
49. Knölker, H.-J.; Braxmeier, T. Synlett 1997, 925-928.
50. -1.
51. (a) Yamada, H.; Shimizu, S.; Yoneda, K. Hakko to Kogyo (Fermentation and Industry) 1980, 38, 937-946.
52. (b) Takahashi, S. Hakko Kogaku (Fermentation Technology) 1983, 61, 139-151.
53. c) Bommarius, A. S.; Schwarm, M.; Drauz, K. J. Mol. Catal. B: Enz. 1998, 5, 1-11.
54. Suzuki, T.; Igarashi, K.; Hase, K.; Tuzimura, K. Agric. Biol. Chem. 1973, 37, 411-416.
55. Morin, A. Enzyme Microb. Technol. 1993, 15, 208-214.
56. 3).
57. Ohi, K.; Shima, K.; Hamada, K.; Saito, Y.; Yamada, N.; Ohba, S.; Nishiyama, S. Bull Chem. Soc. Jpn. 1998, 71, 2433-2440.
58. 3: C, 56.82; H, 4.77; N, 5.52. Found: C, 57.10; H, 4.64; N, 5.47.
59. Willy, W. E.; McKean, D. R.; Garcia, B. A. Bull. Chem. Soc. Jpn. 1976, 49, 1989-1995.
60. 30
61. -1.
62. Bull, S. D.; Davies, S. G.; Jones, S.; Polywka, M. E. C.; Prasad, R. S.; Sanganee, H. J. Synlett 1998, 519-521.
63. Akiba,T.; Tamura, O.; Hashimoto, M.; Kobayashi, Y.; Katoh, T.; Nakatani, K.; Kamada, M.; Hayakawa, I.; Terashima, S. Tetrahedron 1994, 50, 3905-3914.
64. (a) Yamada, H.; Takahashi, S.; Kii, Y.; Kumagai, H. J. Ferment. Technol. 1978, 56, 484-491.
65. (b) Takahashi, S.; Ohashi, T.; Kii, Y.; Kumagai, H.; Yamada, H. J. Ferment. Technol. 1979, 57, 328-332.
66. 31
67. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144.