Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 53804451 | HCID 53804451 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 53822480 | HCID 53822480 | 152.5% |
Reaction Steps
Trifluoroacetic acid (0.58 ml, 7.51 mmol) was added to a solution of the compound (564 mg, 1.50 mmol) prepared in Example 6 in methylene chloride (10 ml) at 0° C. in an argon atmosphere. The mixture was stirred for two hours at this temperature and one hour at room temperature. After the addition of sodium hydrogencarbonate (189 mg, 2.25 mmol), water (7 ml), and ethyl acetate (28 ml), the mixture was stirred at room temperature for 40 minutes and diluted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine in this order and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to obtain 432 mg (yield 73%) of the title compound as a colorless oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06051569 |
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| Source dataset | uspto-grants-2000_04 |
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| ORD ID | ord-89368070293b404c8c9187ea8263da2e |
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| Source note | uspto-grants-2000_04 |
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