| US 7,541,458 B2 | ||
| β-lactam synthesis | ||
| Phong Vu, Little Falls, N.J. (US); and Robert A. Holton, Tallahassee, Fla. (US) | ||
| Assigned to Florida State University Research Foundation, Inc., Tallahassee, Fla. (US) | ||
| Filed on Jun. 08, 2006, as Appl. No. 11/449,462. | ||
| Claims priority of provisional application 60/708929, filed on Aug. 17, 2005. | ||
| Claims priority of provisional application 60/689425, filed on Jun. 10, 2005. | ||
| Prior Publication US 2006/0281914 A1, Dec. 14, 2006 | ||
| This patent is subject to a terminal disclaimer. | ||
| Int. Cl. C07D 205/08 (2006.01) | ||
| U.S. Cl. 540—200 | 18 Claims |
| 1. A process for the preparation of cis-β-lactam (1A), the process comprising treating an imine (2) with a ketene acetal (3A)
in the presence of a siloxide, M+O−SiR51R52R53, to form a reaction product mixture comprising cis- and trans-β-lactams (1A) and (1B), with the ratio of cis-β-lactam (1A)
to trans-β-lactam (1B) in the reaction product mixture being at least 3:1 (cis:trans), wherein
the cis- and trans-β-lactams (1A) and (1B), the imine (2), and the ketene acetal (3A) correspond to Formulae (1A), (1B), (2),
and (3A), respectively:
 M+is a metal ion;
X1a and X1b are trimethylsilyl or X1a and X1b are triethylsilyl;
X3 is phenyl, cyclopropyl, furyl, thienyl, pyridyl, or cyclopentyl;
X6 is trimethylsilyl or triethylsilyl;
and —SiR51R52R53 is trimethylsilyl or triethylsilyl.
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