Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Fluorophenol | HCID 9732 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 59619199 | HCID 59619199 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59619464 | HCID 59619464 | 68.7% |
Reaction Steps
(1R,2R,4R) and (1S,2S,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (25 mg, 0.062 mmol, example 56) was dissolved in DMF (1.5 ml) and 4-fluorophenol (14 mg, 0.125 mmol) and Cs2CO3 (61 mg, 0.187 mmol) were added. The reaction mixture was stirred for 4 h at 50° C. Then water was added and the mixture was extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. The remaining residue was purified by silica gel chromatography (DCM/EtOAc 9:1) to obtain the title compound (21 mg, 63%) as white solid. MS (EI): 491.1 (M−H)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07893099B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-0ae88e00996e4a71b5ea0a4b9571050b |
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| Source note | uspto-grants-2011_02 |
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