Use of an iodonium ylide in the synthesis of p-nitrobenzyl (6R, 7S) 3-hydroxy-8-oxo-7-phenoxyacetamido-1-azabicyclo[4.2.0] octa-2-ene-2-carboxylate

Tetrahedron Letters

Volumn 38, Issue 40, 1997, Pages 6981-6984

  Vaid, Radhe K ^a   Hopkins, Thomas E ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; 3 HYDROXY 8 OXO 7 PHENOXYACETAMIDO 1 AZABICYCLO[4.2.0]OCT 2 ENE 2 CARBOXYLIC ACID 4 NITROBENZYL ESTER; CARBACEPHEM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030807332     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01669-9     Document Type: Article

References (17)

1. Lorabid; Eli Lilly and Company (1991).
2. Cefaclor; Eli Lilly and Company (1991).
3. Evans, D. A.; Sjogren, B., US Patent, 1988, 4,870,169; Bodurow, C.C.; Boyer, B. D.; Brennan, J.; Bunnell, C. A.; Burks, J.; Carr, M. A.; Doecke, C. W.; Eckrich, T.M.; Fisher, J. W.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.;. Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L .L.; Morin J. M.; Nist, R. L.; Prather, D. E.; Sparks, D. L.; Vladuchick, W. C.; Tetrahedron Lett., 1989, 30, 2321.
4. Evans, D. A.; Sjogren, B., US Patent, 1988, 4,870,169; Bodurow, C.C.; Boyer, B. D.; Brennan, J.; Bunnell, C. A.; Burks, J.; Carr, M. A.; Doecke, C. W.; Eckrich, T.M.; Fisher, J. W.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.;. Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L .L.; Morin J. M.; Nist, R. L.; Prather, D. E.; Sparks, D. L.; Vladuchick, W. C.; Tetrahedron Lett., 1989, 30, 2321.
5. Moriarty, R. M.; Prakash, O.; Vaid, R. K.; Zhao, L.; J. Am. Chem. Soc., 1989, 111, 6443; Gallos, J.K.; Koftis, T. V.; Koumbis, A. E.; J. Chem. Soc., Perkin Trans. I, 1994, 611 .
6. Moriarty, R. M.; Prakash, O.; Vaid, R. K.; Zhao, L.; J. Am. Chem. Soc., 1989, 111, 6443; Gallos, J.K.; Koftis, T. V.; Koumbis, A. E.; J. Chem. Soc., Perkin Trans. I, 1994, 611 .
7. Kume, M.; Kubota, T.; Iso, Y.; Tetrahedron Lett., 1994, 36, 8043.
8. Moriarty, R.M.; Vaid R. K.; Synthesis, 1990, 431; Moriarty, R.M.; Vaid, R.K.; Koser, G. F.; SynLett., 1990, 365; Varvoglis, A.; Hypervalent Iodine in Organic Synthesis, Academic Press, London, 1997; Stang P.J.; Zhdankin, V. V.; Chem. Rev., 1996, 96, 1123.
9. Moriarty, R.M.; Vaid R. K.; Synthesis, 1990, 431; Moriarty, R.M.; Vaid, R.K.; Koser, G. F.; SynLett., 1990, 365; Varvoglis, A.; Hypervalent Iodine in Organic Synthesis, Academic Press, London, 1997; Stang P.J.; Zhdankin, V. V.; Chem. Rev., 1996, 96, 1123.
10. Moriarty, R.M.; Vaid R. K.; Synthesis, 1990, 431; Moriarty, R.M.; Vaid, R.K.; Koser, G. F.; SynLett., 1990, 365; Varvoglis, A.; Hypervalent Iodine in Organic Synthesis, Academic Press, London, 1997; Stang P.J.; Zhdankin, V. V.; Chem. Rev., 1996, 96, 1123.
11. Moriarty, R.M.; Vaid R. K.; Synthesis, 1990, 431; Moriarty, R.M.; Vaid, R.K.; Koser, G. F.; SynLett., 1990, 365; Varvoglis, A.; Hypervalent Iodine in Organic Synthesis, Academic Press, London, 1997; Stang P.J.; Zhdankin, V. V.; Chem. Rev., 1996, 96, 1123.
12. 8I requires C51.88, H 3.91, N 6.26, I 18.91.
13. 3) δ: 1.72(m, 1H), 2.00(m, 1H), 2.5(m, 2H), 3.95(m, 1H), 4.56(s, 2H), 5.25, 5.55(d, d, 2H), 5.5.36(dd, 1H), 6.92(d,2H), 7.02(m, 1H), 7.29(m, 3H), 7.60(d, 2H), 8.25(d, 2H), 10.90(s, 1H).
14. O. Neiland; B. Karele, Zh. Organ. Khim., 2, 488, 1966; D. E. Neiman; O. Neiland, Zh. Organ. Khim., 6, 633 (1970).
15. O. Neiland; B. Karele, Zh. Organ. Khim., 2, 488, 1966; D. E. Neiman; O. Neiland, Zh. Organ. Khim., 6, 633 (1970).
16. To a solution of iodonium ylide 5 (0.35gm, 0.0005moles) in methylene chloride and ethanol (10 ml:20 ml) was added acid (0.0016mmol) at room temperature. The reaction contents were stirred for 1hr. and concentrated to an oil. The oil was chromatographed using a silica column, ethyl acetate and hexane (70:30) as eluents. Thus, 6 was obtained in 50% and 53% yields from 4 using methanesulfonic acid and p-toluenesulfonic acid, respectively.
17. Jackson, B. G.; Gardner, J. P.; Heath, P. C.; Tetrahedron Lett., 31, 6317 (1990).