Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Iodoethane | HCID 6340 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 69422764 | HCID 69422764 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69420202 | HCID 69420202 | 97% |
Reaction Steps
Sodium hydride (60%, oily, 28.0 mg) was added to a solution of ethyl 3-[1-[3-hydroxy-5-[2-(2-pyrazinyl)-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionate (378 mg) in N,N-dimethylformamide (5 ml) at 0° C., which was stirred at room temperature for 15 minutes. Iodoethane (0.0672 ml) was added to the mixture, which was stirred at room temperature for 1 hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[1-[3-ethoxy-5-[2-(2-pyrazinyl)-4-thiazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionate (385 mg, yield: 97%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07179823B1 |
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| Source dataset | uspto-grants-2007_02 |
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| ORD ID | ord-3e259acf1f414c22b467cc5d81e35899 |
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| Source note | uspto-grants-2007_02 |
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