Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole | HCID 10236333 | — |
| Reactant | 4-Mercapto-2-propylphenoxy-acetic acid ethyl ester | HCID 20768111 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 9956126 | HCID 9956126 | 55.9% |
Reaction Steps
To a mixture of (4-mercapto-2-propyl-phenoxy)-acetic acid ethyl ester (127 mg, 0.5 mmol) and 4-Chloromethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole (131 mg, 0.48 mmol) in acetonitrile (2 mL) was added cesium carbonate (326 mg, 1 mmol). After 4 h at room temperature, the reaction was quenched by water, extracted with ethyl acetate. Combined organic layers were washed with brine, dried (sodium sulfate) and concentrated. The residue was taken into THF (2 mL) and treated with lithium hydroxide (1N, 0.5 mL) at room temperature for 2 h. THF was evaporated, the residue was treated with water (0.5 mL) and extracted with ether. The aqueous was acidified with 5 N HCl, extracted with ether, dried over sodium sulfate and concentrated. The crude product was purified by reversed phase HPLC to give the title compound (125 mg, 53.7%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06982278B2 |
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| Source dataset | uspto-grants-2006_01 |
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| ORD ID | ord-50406eb7e06e47f2bec567ac384d7370 |
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| Source note | uspto-grants-2006_01 |
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