C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/335.5
C07D 205/08 (2006.01) C07F 7/10 (2006.01) C07F 7/18 (2006.01)
Patent
CA 1278302
Abstract of the Disclosure A process for preparing a 4-acetoxy-3- hydroxyethylazetidin-2-one derivative having the formula (II): Image (II) wherein R1 is a protective group for the hydroxyl group, which comprises reacting a .beta.-lactam compound having the formula (I): Image (I) wherein R1 is as defined above and R2, R3 and R4 are the same or different and each is a lower alkyl group having 1 to 4 carbon atoms or an aralkyl group, with acetic anhydride in the presence of a base and a catalyst selected from the group consisting of an organic strong acid, a mineral acid, a Lewis acid, a halogenated acyl compound having the formula (IV): R8-CO-X (IV) wherein R8 is an alkyl group, an aralkyl group or phenyl group and X is a halogen atom, a halogenated sulfonyl compound having the formula (V): R9-SO2-X (V) wherein R9 is an alkyl group, an aralkyl group or phenyl group and X is a halogen atom, and a compound having the formula (VI): (R10)4-n-Si(X')n (VI) wherein R10 is a lower alkyl group having 1 to 6 carbon atoms or phenyl group, X' is a halogen atom or CF3SO2O group and n is an integer of 1 to 4. According to the present invention, there can be obtained 4-acetoxy-3- hydroxyethylazetidin-2-one derivatives, which are useful intermediates for preparing carbapenem .beta.-lactam antibiotics, in high yield.
559047
Kan Kazunori
Matsumoto Shingo
Ohashi Takehisa
Sada Isao
Ueyama Noboru
Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
Osler Hoskin & Harcourt Llp
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