Trials for the synthesis of (R)-4-mercapto-pyrrolidin-2-one ((R)-MPD)

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 909-912

  Kobayashi, Satoshi ^a   Kobayashi, Katsuhiro ^a   Hirai, Koichi ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

4 hydroxy pyrrolidone; 4 mercapto pyrrolidone; CS 834; Curtius rearrangement; Intramolecular Schmidt reaction; Pig liver esterase; lactam formation

Indexed keywords

4 MERCAPTOPYROLLIDIN 2 ONE; 6 (1 HYDROXYETHYL) 4 METHYL 7 OXO 3 (5 OXO 3 PYRROLIDINYLTHIO) 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID; 6 (1 HYDROXYETHYL) 4 METHYL 7 OXO 3 (5 OXO 3 PYRROLIDINYLTHIO) 1 AZABICYCLO[3.2.0]HEPT 2 ENE 2 CARBOXYLIC ACID PIVALOYLOXYMETHYL ESTER; CARBAPENEM DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; HYDROLYSIS; OPTICAL ROTATION; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033047735     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3111     Document Type: Article

References (26)

1. Tribactams:. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc., 1995, 117, 9604. Ghiron, C.; Rossi, T. Targets in Heterocyclic Systems (Italian Society of Chemistry), 1997, 1, 161. G. Gaviraghi, Eur. J. Med. Chem., 1995, 30 (Supplement), 467. DZ-2640: Nishi, T.; Ishida, Y.; Sugita, K.; Ohtsuka, M.; Takemura, M.; Hayakawa, I., Hayano, T. 35th Intersci. Conf. Antimicrob. Agents Chemother. (Sept 17-20, San Francisco), 1995, Abst. F-133. L-084: Abe, T.; Hayashi, K.; Mihira, A.; Satoh, C.; Tamai, S.; Yamamoto, S.; Hikida, M.; Kumagai, T.; Kitamura, M. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego), 1998, Abst. F-64. TA-949: Seki, M.; Kondo, K.; Iwasaki, T. 13th French-Japanese Symposium on Medicinal and Fine Chemistry (May 25-28, Hayama), 1998, Abst. P-12.
2. Tribactams:. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc., 1995, 117, 9604. Ghiron, C.; Rossi, T. Targets in Heterocyclic Systems (Italian Society of Chemistry), 1997, 1, 161. G. Gaviraghi, Eur. J. Med. Chem., 1995, 30 (Supplement), 467. DZ-2640: Nishi, T.; Ishida, Y.; Sugita, K.; Ohtsuka, M.; Takemura, M.; Hayakawa, I., Hayano, T. 35th Intersci. Conf. Antimicrob. Agents Chemother. (Sept 17-20, San Francisco), 1995, Abst. F-133. L-084: Abe, T.; Hayashi, K.; Mihira, A.; Satoh, C.; Tamai, S.; Yamamoto, S.; Hikida, M.; Kumagai, T.; Kitamura, M. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego), 1998, Abst. F-64. TA-949: Seki, M.; Kondo, K.; Iwasaki, T. 13th French-Japanese Symposium on Medicinal and Fine Chemistry (May 25-28, Hayama), 1998, Abst. P-12.
3. Tribactams:. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc., 1995, 117, 9604. Ghiron, C.; Rossi, T. Targets in Heterocyclic Systems (Italian Society of Chemistry), 1997, 1, 161. G. Gaviraghi, Eur. J. Med. Chem., 1995, 30 (Supplement), 467. DZ-2640: Nishi, T.; Ishida, Y.; Sugita, K.; Ohtsuka, M.; Takemura, M.; Hayakawa, I., Hayano, T. 35th Intersci. Conf. Antimicrob. Agents Chemother. (Sept 17-20, San Francisco), 1995, Abst. F-133. L-084: Abe, T.; Hayashi, K.; Mihira, A.; Satoh, C.; Tamai, S.; Yamamoto, S.; Hikida, M.; Kumagai, T.; Kitamura, M. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego), 1998, Abst. F-64. TA-949: Seki, M.; Kondo, K.; Iwasaki, T. 13th French-Japanese Symposium on Medicinal and Fine Chemistry (May 25-28, Hayama), 1998, Abst. P-12.
4. Tribactams:. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc., 1995, 117, 9604. Ghiron, C.; Rossi, T. Targets in Heterocyclic Systems (Italian Society of Chemistry), 1997, 1, 161. G. Gaviraghi, Eur. J. Med. Chem., 1995, 30 (Supplement), 467. DZ-2640: Nishi, T.; Ishida, Y.; Sugita, K.; Ohtsuka, M.; Takemura, M.; Hayakawa, I., Hayano, T. 35th Intersci. Conf. Antimicrob. Agents Chemother. (Sept 17-20, San Francisco), 1995, Abst. F-133. L-084: Abe, T.; Hayashi, K.; Mihira, A.; Satoh, C.; Tamai, S.; Yamamoto, S.; Hikida, M.; Kumagai, T.; Kitamura, M. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego), 1998, Abst. F-64. TA-949: Seki, M.; Kondo, K.; Iwasaki, T. 13th French-Japanese Symposium on Medicinal and Fine Chemistry (May 25-28, Hayama), 1998, Abst. P-12.
5. Tribactams:. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc., 1995, 117, 9604. Ghiron, C.; Rossi, T. Targets in Heterocyclic Systems (Italian Society of Chemistry), 1997, 1, 161. G. Gaviraghi, Eur. J. Med. Chem., 1995, 30 (Supplement), 467. DZ-2640: Nishi, T.; Ishida, Y.; Sugita, K.; Ohtsuka, M.; Takemura, M.; Hayakawa, I., Hayano, T. 35th Intersci. Conf. Antimicrob. Agents Chemother. (Sept 17-20, San Francisco), 1995, Abst. F-133. L-084: Abe, T.; Hayashi, K.; Mihira, A.; Satoh, C.; Tamai, S.; Yamamoto, S.; Hikida, M.; Kumagai, T.; Kitamura, M. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego), 1998, Abst. F-64. TA-949: Seki, M.; Kondo, K.; Iwasaki, T. 13th French-Japanese Symposium on Medicinal and Fine Chemistry (May 25-28, Hayama), 1998, Abst. P-12.
6. Tribactams:. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc., 1995, 117, 9604. Ghiron, C.; Rossi, T. Targets in Heterocyclic Systems (Italian Society of Chemistry), 1997, 1, 161. G. Gaviraghi, Eur. J. Med. Chem., 1995, 30 (Supplement), 467. DZ-2640: Nishi, T.; Ishida, Y.; Sugita, K.; Ohtsuka, M.; Takemura, M.; Hayakawa, I., Hayano, T. 35th Intersci. Conf. Antimicrob. Agents Chemother. (Sept 17-20, San Francisco), 1995, Abst. F-133. L-084: Abe, T.; Hayashi, K.; Mihira, A.; Satoh, C.; Tamai, S.; Yamamoto, S.; Hikida, M.; Kumagai, T.; Kitamura, M. 38th Intersci. Conf. Antimicrob. Agents Chemother., (Sept 24-27, San Diego), 1998, Abst. F-64. TA-949: Seki, M.; Kondo, K.; Iwasaki, T. 13th French-Japanese Symposium on Medicinal and Fine Chemistry (May 25-28, Hayama), 1998, Abst. P-12.
7. Kawamoto, I.; Miyauchi, M.; Endo, R.; Hisaoka, M.; Yasuda, H.; Kuwahara, S. 36th Intersci. Conf. Antimicrob. Agents Chemother., (New Orleans), 1996, Abst. F-105. Miyauchi, M.; Endo, R.; Hisaoka, M.; Yasuda, H.; Kawamoto, I. J. Antibiot., 1997, 50, 429.
8. Kawamoto, I.; Miyauchi, M.; Endo, R.; Hisaoka, M.; Yasuda, H.; Kuwahara, S. 36th Intersci. Conf. Antimicrob. Agents Chemother., (New Orleans), 1996, Abst. F-105. Miyauchi, M.; Endo, R.; Hisaoka, M.; Yasuda, H.; Kawamoto, I. J. Antibiot., 1997, 50, 429.
9. Kobayashi, K.; Fukuhara, H.; Takebayashi, T.; Kawamoto, I. Japan Kokai Tokkyo Koho JP 96-119935, May 14, 1996 (Priority Claim, Aug. 31, 1994).
10. (S)-hydroxy-GABA is now commercially available from DAISO Co., Ltd. (Japan). Pellegata, R.; Pinza, M.; Pifferi, G. Synthesis, 1978, 614.
11. Norris, P.; Horton, D.; Levine, B. R. Tetrahedron Lett., 1995, 36, 7811.
12. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron, 1984, 30, 2151. Ninomiya, K.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull., 1974, 22, 1398.
13. Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron, 1984, 30, 2151. Ninomiya, K.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull., 1974, 22, 1398.
14. Donnelly, D. M. X.; Finet, J.-P.; Rattigan, B. A. J. Chem. Soc., Perkin Trans. 1, 1993, 1729.
15. Nakada, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett., 1988, 32, 3951. Nakada, M.; Kobayashi, S.; Iwasaki, S.; Ohno, M. Tetrahedron Lett., 1993, 34, 1035 and references cited therein.
16. Nakada, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett., 1988, 32, 3951. Nakada, M.; Kobayashi, S.; Iwasaki, S.; Ohno, M. Tetrahedron Lett., 1993, 34, 1035 and references cited therein.
17. Evans, D. A.; Black, W. C. J. Am. Chem. Soc., 1993, 115, 4497
18. Theisen, P. D.; Heathcock, C. H. J. Org. Chem., 1993, 58, 142; J. Org. Chem., 1988, 53, 2374.
19. Theisen, P. D.; Heathcock, C. H. J. Org. Chem., 1993, 58, 142; J. Org. Chem., 1988, 53, 2374.
20. f = 0.40 (AcOEt).
21. 3) δ:2.59-2.70 (4H, m), 3.36-3.43 (1H, m), 3.68 (3H, s), 3.77 (2H, s), 3.79 (3H, s), 6.84 (2H, d, J = 8.8 Hz), 7.25 (2H, d, J = 8.8 Hz).
22. 3) δ:2.60-2.75 (4H, m), 3.34-3.41 (1H, m), 3.68 (3H, s), 3.78 (2H, s), 3.79 (3H, s), 6.84 (2H, d, J = 8.7 Hz), 7.24 (2H, d, J = 8.7 Hz).
23. 3) δ: 2.50-2.62 (2H, m), 3.09-3.16 (1H, m), 3.30-3.33 (2H, m), 3.68 (3H, s), 3.74 (2H, s), 3.79 (3H, s), 4.54 (2H, d, J = 5.4 Hz), 5.05 (1H, br), 5.22 (1H, dd, J = 11.1, 1.3 Hz), 5.30 (1H, dd, J = 17.5, 1.3 Hz), 5.91 (1H, ddt, J = 17.5, 11.1, 5.4 Hz), 6.85 (2H, d, J = 8.7 Hz), 7.24 (2H, d, J = 8.7 Hz).
24. 3) δ: 2.27 (1H, dd, J = 17.0, 7.2 Hz), 2.59 (1H, dd, J = 17.0, 8.6 Hz), 3.22 (1H, dd, J = 10.1, 6.0 Hz,), 3.35-3.42 (1H, m), 3.56 (1H, dd, J = 10.1, 7.2 Hz), 3.73 (2H, s), 3.80 (3H, s), 6.38 (1H, br), 6.85 (2H, A, J = 8.7 Hz), 7.22 (2H, d, J = 8.7 Hz).
25. D+36.5° (c = 1.179, MeOH). mp. 69.5-70 °C.
26. 3) δ: 1.60 (3H, d, J = 5.5 Hz), 2.62 (2H, d, J = 6.5 Hz), 2.67 (2H, d, J = 7.5 Hz), 3.2-3.6(1H, m), 3.71 (3H, s), 6.08 (1H, q, J = 6.0 Hz), 6.69 (2H, d, J = 9.1 Hz), 7.10 (2H, d, J = 9.1 Hz), 7.30-7.95 (7H, m), 8.20 (1H, br).