Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 86675921 | HCID 86675921 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86675920 | HCID 86675920 | 87.5% |
Reaction Steps
To a stirred solution of (2S,5R)-5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxane-2-carboxylic acid (0.3 g, 0.632 mmol, Example #P.1) in DMF (2 mL) was added potassium carbonate (0.131 g, 0.948 mmol) followed by iodomethane (0.108 g, 0.759 mmol). The reaction mixture was stirred at RT for about 3 h. The reaction mixture was quenched with water (15 mL), the product separated as solids and collected by filtration, washed with water (10 mL) and dried under vacuum to obtain (2S,5R)-methyl 5-((S)-3-(6-(4-fluoro-3-methoxybenzylcarbamoyl)-2-methylpyrimidin-4-yl)-4,5-dihydroisoxazol-5-yl)-1,4-dioxane-2-carboxylate 0.270 g, (87%), ES-MS: m/z 489 (m+H)+, LC/MS (Table 1, method d) Rt=2.25 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09029409B2 |
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| Source dataset | uspto-grants-2015_05 |
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| ORD ID | ord-6cce3cb2bb934cbabd92c84031ca6c18 |
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| Source note | uspto-grants-2015_05 |
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