NEW MATERIAL:The compound of formula I (R1 is formyl, carboxyl or acetyloxy; R2 is H or N-protecting group).
EXAMPLE: (3R,4S)-3-[(R)-1-fluoroethyl]4-formyl-1-(p-methoxy)phenyl-2-azetidinone.
USE: Medicine. It has excellent antibacterial activity and is useful as a synthetic intermediate for carbapenam or carbapenem antibiotic substance such as the antibiotic substance of formula II safe to renal dehydropeptitase and useful as an antibacterial agent.
PREPARATION: A compound of formula I wherein R1 is formyl and R2 in N- protecting group can be produced by (1) reacting the compound of formula III (R3 is lower alkyl) with the compound of formula IV (R21 is N-protecting group) in the presence of lithium diisopropylamide of formula V, etc., (2) fluorinating the resultant compound of formula VI with diethylaminosulfate trifluoride of formula VII and (3) oxidizing the obtained compound of formula VIII with ozone.
SENDA NORITAKA
WATANABE AZUMA
FUKAGAWA YASUO
ISHIKURA TOMOYUKI
| JPS59216886A | 1984-12-06 | |||
| JPS60149587A | 1985-08-07 | |||
| JPS58103358A | 1983-06-20 | |||
| JPS6048964A | 1985-03-16 |