4-Acetoxy-2-azetidinone synthesis
- Product Name:4-Acetoxy-2-azetidinone
- CAS Number:28562-53-0
- Molecular formula:C5H7NO3
- Molecular Weight:129.11
108-05-4
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28562-53-0
The reaction of chlorosulfonyl isocyanate (1.0 mL, 11 mmol) with vinyl acetate (5.0 mL, 54 mmol) in anhydrous dichloromethane for 2 h at 0 °C afforded 4-acetoxy-2-azetidinone (Compound 9, 0.50 g, 35% yield). The spectral data of compound 9 was in agreement with the results reported in the literature.
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Yield: 65%
Reaction Conditions:
with peracetic acid;acetic acid
Steps:
54 Synthesis of 4-acetoxyazetidine-2-one
EXAMPLE 54 Synthesis of 4-acetoxyazetidine-2-one 1.42 g (20 mmol) of azetidine-2-one was added with 1.81 g (22 mmol) of anhydrous sodium acetate, 6.4 g of acetic acid, 5.6 g of ethyl acetate and 0.678 g (2 mmol) of benzene ruthenium dibromide, cooled to 5°-10° C., then added dropwise with 16.5 g of acetic acid solution containing 22% peracetic acid over 1.5 hours while stirring. After the dropping, a further 15 hour stirring was conducted at the same temperature. The solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (hexane/ethyl acetate=1/1 by volume) to obtain 1.67 g of 4-acetoxyazetidine-2-one (yield: 65%).
References:
Takasago International Corporation US5204460, 1993, A
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28562-53-0
155 suppliers
$9.00/250mg