Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4-Fluoro-4'-hydroxybiphenyl | HCID 345420 | — |
| Reactant | 2-{[4-(Chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester | HCID 58451403 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58451400 | HCID 58451400 | — |
Reaction Steps
2-{[4-(Chloroacetyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (23.8 g) and 4′-fluorobiphenyl-4-ol (12.00 g) obtained in Example 1 were dissolved in toluene (650 mL), aqueous sodium hydroxide solution (1 mol/L, 71 mL), tetrabutylammonium iodide (2.62 g) and water (71 mL) were added, and the mixture was heated under reflux for 3 hr, and allowed to cool to perform partitioning. The organic layer was washed twice with 1 mol/L aqueous sodium hydroxide solution (300 mL) and twice with saturated aqueous sodium chloride solution (200 mL), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Moritex Purif Pack SI 60 μm size 200 was used. elution solvent: hexane/ethyl acetate=95/5→70/30) to give the title compound as a pale-yellow oily substance (1.128 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08497382B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-37688475c70d4f4bac864351f8340bda |
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| Source note | uspto-grants-2013_07 |
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