Uses
tert-Butyl 3-oxoazetidine-1-carboxylate(1-Boc-3-azetidinone) is a currently common organic intermediate. It is a key intermediate for preparing various
medicaments. It can be used for preparing Janus kinase 3(JAKS), which is
a useful target for immunosuppression and transplant rejection, and can
be used for treating inflammatory disorders, autoimmune disorders,
cancer and other diseases; also useful in the preparation of a second
class of HCV protease inhibitors useful in the treatment of HCV genotype
1 infection; can also be used for preparing novel aminoglycoside
compounds with antibacterial activity; bicyclic himbacine (himbacine)
derivatives can be prepared which are useful as antagonists of the
protease activated receptor-1 (PAR-1) and are predicted to be cannabis
(CB2) receptor inhibitors, useful for the treatment of secondary
prevention of Acute Coronary Syndrome (ACS), myocardial infarction or
thrombotic stroke or peripheral arterial disease; bicyclic
azacyclobenzylamine derivatives, such as pyridopyrimidines, can be
prepared that modulate the activity of phospho-inositol 3-kinase (P13K)
and are useful in the treatment of diseases associated with P13K,
including, for example, inflammatory disorders, immune-based disorders,
cancer, and other diseases.
Synthesis
The traditional preparation method of
tert-Butyl 3-oxoazetidine-1-carboxylate is mainly to oxidize the hydroxyl
on an aza ring into ketone. For example: 3-azetidinium alkoxide, di-tert-butyl dicarbonate and
sodium bicarbonate in dioxane: stirring the mixture of water for 15
hours to obtain 3-hydroxyazetidine-1-carboxylic acid-1, 1-dimethylethyl
ester; dissolving 3-hydroxyazetidine-1-carboxylic acid-1, 1-dimethyl
ethyl ester in ethanedioyl chloride and dichloromethane, adding DMSO and
triethylamine, stirring at room temperature for 15 hours to obtain tert-Butyl 3-oxoazetidine-1-carboxylate.
