Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | HCID 23114575 | HCID 23114575 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58734256 | HCID 58734256 | 80% |
Reaction Steps
Under an argon atmosphere, diphenylphosphoryl azide (2.9 ml, 13.6 mmol) and triethylamine (2.7 ml, 19.4 mmol) were added to a solution of 4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]-5-methylpicolinic acid (2.8 mg, 6.40 mmol) in a mixture of t-butanol (20 ml) and toluene (40 ml). The resulting mixture was stirred for 16 hours under heating and refluxing. After cooling, ethyl acetate was added to the reaction mixture. The resulting mixture was washed sequentially with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was washed sequentially with hexane and ethyl acetate to give the title compound (2.60 g, 5.11 mmol, 80%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932271B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-d514787682744336b64228a1e46c6af1 |
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| Source note | uspto-grants-2011_04 |
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