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CAS No. : | 1191252-49-9 | MDL No. : | MFCD25977119 |
Formula : | C22H15Br2N3O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DSFNLJXHXBIKDS-UHFFFAOYSA-N |
M.W : | 545.18 | Pubchem ID : | 135565181 |
Synonyms : |
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Chemical Name : | 3-(3,5-Dibromo-4-hydroxyphenyl)-N-(4-phenoxybenzyl)-1,2,4-oxadiazole-5-carboxamide |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
20% | [0232] Compound 4 was phosphorylated as schematically shown above. To a solution of compound 4 (4.62 g, 8.47 mmol) in THF (50 mL) was added di-tert-butyl N, N- diisopropylphosphoramidite (5.4 mL, 16.9 mmol) and tetrazole (1.78 g, 25.41 mmol). The reaction was stirred at room temp for 3 h then cooled to -40C and treated with a solution of 3-chloroperoxybenzoic acid (85%, 2.06 g, 10.16 mmol) in CH2C 12 (50 mL). The reaction was stirred for 15 min then partitioned between EtOAc (50 mL) and 10% aqueous Na2S203 (75 mL). The organic layer was then washed with 10% aqueous Na2S203 (50 mL), saturated NaHC03 (50 mL), and brine (75 mL). The organic layer was then dried (MgSC^), filtered, and evaporated. The crude product was purified by flash column chromatography (silica, 50% EtOAc/hexane) to yield the desired phosphate 7 (1 .27 g, 20%) as a pale-yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | [0230] Compound 4 (109 mg, 0.2 mmol) was dissolved in dimethylformamide (5 mL), and sodium hydride (60% suspension in mineral oil, 8 mg, 0.2 mmol) was added to it. The resulting solution was stirred for 45 min at room temperature and a solution of phosphoric acid di-tert-butyl ester chloromethyl ester (compound 3, 62 mg, 0.24 mmol) in dimethylformamide (2.5 mL) was slowly added. The reaction was stirred overnight at 50C. The mixture was then diluted with dichloromethane (60 mL). The organic phase was washed with water (30 mL), aqueous saturated NaHC03 (30 mL), and brine (two times 20 mL), dried over Na2S04, and filtered. The crude product was purified by flash column chromatography (silica, 50% Ethyl acetate (EtOAc)/hexane) to yield the desired phosphate compound 5 (61 mg, 40% yield) as a pale-yellow oil. |