Structure of 1192-07-0
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1192-07-0 |
Formula : | C3H5NO2 |
M.W : | 87.08 |
SMILES Code : | O=C1NOCC1 |
MDL No. : | MFCD11878032 |
InChI Key : | QXDOFVVNXBGLKK-UHFFFAOYSA-N |
Pubchem ID : | 192737 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; bis-(trimethylsilyl)acetamide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; benzene; | (11) A mixture of <strong>[1192-07-0]3-isoxazolidinone</strong> (700 mg) in tetrahydrofuran (30 ml) of phosgene (0.018 mole) was stirred at 0-5 C. for 3.5 hours and the solvent was removed. Tetrahydrofuran was added to the residue and the solvent was again removed. The residue was dissolved in benzene and benzene was removed by decantation, and the residue was further evaporated and dissolved in methylene chloride (5 ml). The resultant solution containing 3-oxo-2-isoxazolidinecarbonyl chloride was dropwise added to a solution of 7-(D-2-phenylglycinamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid (2.0 g) and bis(trimethylsilyl)acetamide (3.2 g) in methylene chloride (50 ml) at 0-5 C. and the resultant mixture was stirred at 0-5 C. for 1.5 hour and at room temperature for an hour. After removal of the solvent, the residue was added to ethyl acetate (70 ml) and 5% hydrochloric acid (40 ml) and an insoluble substance was filtered off. The organic layer was washed with 5% hydrochloric acid and water and dried, and the solvent was distilled off under reduced pressure. The residue was pulverized with diethyl ether, the resultant crude powder (1.40 g) was treated with active charcoal in acetone and acetone was removed. The residue was pulverized with diethyl ether to give powder (0.94 g) of 7-[D-2-(3-oxo-2-isoxazolidinecarboxamido)-2-phenylacetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid, mp 138 to 144 C. (dec). |