A practical synthesis of 3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(2R)- 4-halo-3-oxo-2-butyl]azetidinone, a versatile intermediate for carbapenem antibiotics.
A key intermediate for 2-(functionalized-methyl)-1-beta-methylcarbapenems, 3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(2R)- 4-halo-3-oxo-2-butyl]azetidinone, was prepared efficiently from a commercially available carboxylic acid in 3 steps.
Yang
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C
Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, USA.
Yasuda
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N
D001384:Azetidines / Q000737:chemistry*; D015780:Carbapenems / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D017646:Organosilicon Compounds / Q000737:chemistry*
C116735:3-(1-tert-butyldimethylsilyloxyethyl)--4-(4-chloro-3-oxo-2-butyl)azetidinone; C116734:3-(1-tert-butyldimethylsilyloxyethyl)-4-(4-bromo-3-oxo-2-butyl)azetidinone; D001384:Azetidines; D015780:Carbapenems; D007202:Indicators and Reagents; D017646:Organosilicon Compounds