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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 17, Number 4
BKCSDE 17(4)
April 20, 1996 

 
Title
Synthesis of 3-[1-(t-Butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone Derivatives
Author
Min Hyo Seo, Youn Young Lee*, Yang Mo Goo
Keywords
Abstract
Isoxazolidine derivatives 7 and 8 were synthesized from N-benzyl-C-(2-benzyloxyethyl)nitrones by 1,3-dipolar cycloaddition with ethyl crotonate. The isoxazolidine derivatives were converted to β -amino acid esters 9a and 9b by reduction with zinc in acetic acid. The β-amino acid esters were reacted with methylmagnesium bromide to give the 2-azetidinones (13a, 13b). The benzyl group of 2-azetidinones were removed by Birch reduction. The products were oxidized with PDC to give 3-[1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymeth yl-2-azetidinone derivatives (2a, 2c).
Page
314 - 321
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