Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1H-1,2,4-Triazole | HCID 9257 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 15337568 | HCID 15337568 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 10041670 | HCID 10041670 | 42.3% |
Reaction Steps
1H-1,2,4-Triazole (41 mg) was added an ice-cooled dispersion of 60% sodium hydride in oil (23 mg) in dimethylformamide (1 ml) and the resulting mixture was stirred for 10 minutes at room temperature. To the mixture was added a solution of (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(2H-1,2,3-triazol-2-yl)ethyl]oxirane (76 mg) in dimethylformamide (0.8 ml), followed by heating for 5 hours at 50° C. and cooling. To the reaction mixture was added cold water (5 ml) and ethyl acetate (15 ml). The separated aqueous layer was extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was subjected to silica gel column chromatography (acetone/dichlormethane=1:2→1:1). The obtained oily substance was crystallized from isopropyl ether to give the title compound (Compound 8, 41 mg, 42%) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05371100 |
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| Source dataset | uspto-grants-1994_12 |
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| ORD ID | ord-6e1014108c934af987dc1494d85d2058 |
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| Source note | uspto-grants-1994_12 |
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