Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 43589287 | HCID 43589287 | — |
| Reactant | Tert-butyl 5-biphenyl-4-yl-3-oxopentanoate | HCID 58914664 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 69242505 | HCID 69242505 | 52.2% |
Reaction Steps
To a solution of the compound (300 mg) obtained from step 1 above in dry tetrahydrofuran (4 ml) and tert-butanol (4 ml) at 0° C. was added potassium tert-butoxide (104 mg) and stirred for 20 minutes. To the resulting reaction mixture was added 3-(2-bromoethyl)-1,2,3-benzotriazin-4(3H)-one (235 mg) and tetrabutylammonium iodide (349 mg) and the mixture was further stirred for 30 minutes at 0° C., followed by stirring at room temperature for 30 minutes and finally at 80° C. for about 5-6 hours. The solvent was evaporated under reduced pressure and the residue thus obtained was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulphate and filtered. The solvent was evaporated under reduced pressure and the residue thus obtained was purified by column chromatography using 20% ethyl acetate in hexane as eluant to furnish the title compound (240 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08710261B2 |
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| Source dataset | uspto-grants-2014_04 |
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| ORD ID | ord-d6ea9cdf44dd4640bbd9042fccb4732c |
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| Source note | uspto-grants-2014_04 |
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