Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-(3-Hydroxy-4-methoxy-benzoylamino)-4-trifluoromethyl-cyclohexanecarboxylic Acid Methyl Ester | HCID 67171129 | — |
| Reactant | HCID 86672565 | HCID 86672565 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67169158 | HCID 67169158 | 90.2% |
Reaction Steps
60 mg of 1-(3-Hydroxy-4-methoxy-benzoylamino)-4-trifluoromethyl-cyclohexanecarboxylic acid methyl ester, 53 mg of toluene-4-sulfonic acid 2-(3-oxetan-3-yl-phenyl)-ethyl ester, and 66 mg of K2CO3 were added to 3 ml of DMF and the mixture was stirred for 8 h at 40° C. Then, 27 mg of toluene-4-sulfonic acid 2-(3-oxetan-3-yl-phenyl)-ethyl ester were added and stirring was continued for 8 h at 40° C. Then, 10 ml of EA and 15 ml of a half-saturated aqueous NaCl-solution were added. The layers were separated and the aqueous layer was extracted twice using 10 ml of EA each. The combined organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:1 yielded 77 mg of the title compound, amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618304B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-4f6a8136f97a44cba30ec72c128fc212 |
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| Source note | uspto-grants-2013_12 |
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