Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate | HCID 86665320 | — |
| Reactant | HCID 131731101 | HCID 131731101 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 68748821 | HCID 68748821 | — |
Reaction Steps
Under the argon atmosphere, the compound (165 mg) produced in Example 100 was dissolved in DME (2 mL), the solution was cooled to −78° C., followed by addition of a 0.5M potassium hexamethyldisilazane/toluene solution (0.90 mL). After stirring the mixture at −78° C. for 20 minutes, a DME (1.5 mL) solution of the compound produced in Example 13 was added dropwise, and stirring at the same temperature was carried out for 10 minutes. After raising a temperature of the reaction solution to 0° C., water was added, and the extract obtained by extraction with ethyl acetate was washed with water and a saturated saline; dried with anhydrous magnesium sulfate; and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→65:35) to obtain a titled compound (177 mg) having the following physical property values.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09029574B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-b2c2da4a66d94051b2baa9799b389246 |
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| Source note | uspto-grants-2015_05 |
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