Method of preparing a derivative of optically active azetidin-2-

Details Method of preparing a derivative of optically active azetidin-2- Method of preparing a derivative of optically active azetidin-2-

1996-05-13

1998-01-27

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

C07D20508

Patent

active

057123888

ABSTRACT:
To prepare the compound (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one, (2S,3R)-2-aminomethyl-3-hydroxybutyric acid is reacted with an alcohol in the presence of at least one compound chosen from the group consisting of thionyl chloride, hydrogen chloride and p-toluene sulfonic acid, thereby obtaining a salt of the corresponding ester. The salt is reacted with a tri-substituted silane in the presence of a metallic catalyst, thereby protecting the hydroxy group of the ester and then reacted with a base, thereby obtaining an ester of (2S,3R)-2-aminomethyl-3-(tri-substituted silyloxy)butyric acid. Subsequently, the ester is transformed into lactam in the presence of a Grignard reagent or a metal amide, thereby obtaining (1'R,3S)-3-(1'-tri-substituted silyloxyethyl)azetidin-2-one. This compound provides a useful base for preparing .beta.-lactam type antimicrobial agents such as carbapenem type agents.

REFERENCES:
patent: 4981992 (1991-01-01), Sayo et al.
patent: 5204461 (1993-04-01), Murayama et al.
patent: 5241064 (1993-08-01), Murata et al.
patent: 5463047 (1995-10-01), Schneider et al.

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