Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 67097895 | HCID 67097895 | — |
| Reactant | HCID 67098073 | HCID 67098073 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67098162 | HCID 67098162 | 21.4% |
Reaction Steps
To a solution of tert-butyl [2-(4-bromophenyl)ethyl]-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (331 mg) in 1,4-dioxane (3.3 ml) were added [4-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-3-isopropoxyphenyl]boronic acid (325 mg), tetrakis(triphenylphosphine)palladium (91 mg) and aqueous solution of sodium carbonate (2M, 1.4 ml), and the mixture was stirred at 80° C. for 3 hours under nitrogen. The mixture was portioned into a mixture of ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/methanol=100/3) to give tert-butyl [2-[4′-[[[(3-hydroxypropyl)sulfonyl]amino]carbonyl]-3′-isopropoxy-4-biphenylyl]-ethyl][(2R)-2-hydroxy-2-(3-pyridyl)ethyl]carbamate (108 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07928264B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-d5517b2ddbd14d32a7f8b96e96c2eaa8 |
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| Source note | uspto-grants-2011_04 |
|---|