Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 59331321 | HCID 59331321 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59331307 | HCID 59331307 | 43.4% |
Reaction Steps
To a solution of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-[(2R,3R,7R)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]ethyl}-1H-pyrrol-2-yl)-1,3-thiazole (0.100 g) in 1,4-dioxane (2 mL) was added 4.5M aqueous sulfuric acid solution (2 mL) at room temperature, and the mixture was stirred at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-80:20, volume ratio), and recrystallized from diethyl ether-hexane to give the title compound (0.03 g, yield 43%) as colorless crystals. MS: 441 (MH+). melting point 165-167° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318746B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-661aaf3ddd694004852239b70479c642 |
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| Source note | uspto-grants-2012_11 |
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