NEW MATERIAL:A (2R,5R)-3-oxo-7-oxo-1-azabicyclo[3. 2. 0]heptane-2-carboxylic acid shown by the formula I (R is H, protecting group, or salt-forming cation).
EXAMPLE: Diphenylmethyl-(2R,5R)-3,7-dioxo-1-azabicyclo[3. 2. 0]heptane-2-carboxylate.
USE: An intermediate for synthesizing carbapenems. An inhibitor for β-lactamase.
PROCESS: R2 or a novel compound shown by the formula II (R1 and R2 are protecting groups) is removed in the presence of an oxidizing agent (e.g., DDQ) to give a compound shown by the formula III, which is subjected to ring closure in the presence of a catalyst (e.g., rhodium acetate), and , if necessary, R1 is removed, or chlorine or a protecting group is introduced after the removal of R1, to give a compound shown by the formula I. The novel compound shown by the formula II is obtained by removing one or both of the protecting groups R3 and R4 of a compound shown by the formula IV, followed by decarboxylation, to give a compound shown by the formula V, which is diazotized.
JP2000344774 | PRODUCTION OF CARBAPENEM COMPOUND |
JPH05320171 | 1-BETA-METHYLCARBAPENEM ANTIBIOTIC INTERMEDIATE |
WO/1990/011284 | ANTIBACTERIAL 2-CARBAPENEM DERIVATIVES |
IKODA NOBUO
SHIBATA HISANARI
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