Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 58065478 | HCID 58065478 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58065449 | HCID 58065449 | 74% |
Reaction Steps
Lithium aluminum hydride (17.0 mg, 0.448 mmol) was suspended in tetrahydrofuran (2 mL). Methyl 2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-4,5-dihydro-1,3-oxazole-5-carboxylate (77.0 mg, 0.146 mmol) synthesized in Example (27b) was dissolved in tetrahydrofuran (2 mL), followed by dropwise addition at 0° C. under nitrogen atmosphere. After stirring at 0° C. for 30 minutes, water (17 μL) and an aqueous sodium hydroxide solution (5M, 68 μL) were added dropwise slowly and sequentially. After filtration through Celite, the solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%) to afford the desired compound (54.1 mg, yield 74%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08415359B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-e5042a2688d647158d38e8e019a68707 |
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| Source note | uspto-grants-2013_04 |
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