Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | HCID 4982676 | HCID 4982676 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Tetrahydrofuran heptane ethylbenzol | HCID 22742125 | — |
| Product | HCID 23120833 | HCID 23120833 | — |
Reaction Steps
Biphenyl-4-sulfonic acid (6-methyl-pyridin-2-yl)-amide (0.5 g, product of example 5) under an argon atmosphere in THF (5 mL) was cooled to −20° C. and treated dropwise at −20° C. with 1.54 mL of a 2 M solution of lithium diisopropylamide in THF/heptane/ethylbenzene (Fluka). The solution was stirred 1 h at −20° C., cooled to −70° C. and then treated with an access of dry ice. The mixture was allowed to warm to RT (1 h), partitioned between diluted aqueous HCl and AcOEt. The layers were separated, the aqueous layer extracted twice with AcOEt, the combined organic layers dried over Na2SO4, filtered and evaporated to give [6-(biphenyl-4-sulfonylamino)-pyridin-2-yl]-acetic acid as light yellow gum (0.779 g) that was used without further purification in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07482341B2 |
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| Source dataset | uspto-grants-2009_01 |
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| ORD ID | ord-25fdac697bea4ca9bd93c8964ad061cb |
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| Source note | uspto-grants-2009_01 |
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