Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Sesamol | HCID 68289 | — |
| Reactant | Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl ester | HCID 12992442 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 21902076 | HCID 21902076 | 61.4% |
Reaction Steps
To a solution of 43 (1.0 g, 2.59 mmol) in acetonitrile (25 mL) was added sesamol (0.36 g, 2.59 mmol) and cesium carbonate (1.27 g, 3.89 mmol). The reaction was stirred and refluxed for 20 h. After cooling to room temperature, the reaction mixture was filtered and most of the solvent was removed by rotary evaporation. The residue was partitioned between dichloromethane and water, and the organic layer was washed with sat. sodium carbonate (2×50 mL) and water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography on silica gel, eluting with dichloromethane/methanol (98:2) to give 0.68 g of the amide 44 as a crystalline solid. C24H26ClNO4, MS (m/z)=428 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07294637B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-8be48956bb83424dab7574cf97a6acb9 |
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| Source note | uspto-grants-2007_11 |
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