Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | 2-Chlorophenol | HCID 7245 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | HCID 66654135 | HCID 66654135 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66653900 | HCID 66653900 | 37.6% |
Reaction Steps
To a degassed solution of 3-[2-(4-iodo-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (0.40 g; 0.92 mmol), and 2-chlorophenol (0.28 g; 2.22 mmol) in DMSO, was added picolinic acid (22.7 mg; 0.18 mmol), CuI (17.6 mg; 0.09 mmol) and K3PO4 (0.78 g; 3.69 mmol). The resulting mixture was heated overnight, at 90° C. After cooling to RT, water was added and the mixture extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, Et2O/hexanes 1:2) to afford 3-{2-[4-(2-Chloro-phenoxy)-phenyl]-thiomorpholin-4-yl}-propionic acid tert-butyl ester (0.15 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09227960B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-49a654ba66624842b38586dc60fd6464 |
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| Source note | uspto-grants-2016_01 |
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