Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl isocyanate | HCID 8022 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | [3-(Bromomethyl)oxetan-3-yl]methanol | HCID 529264 | — |
| Reactant | HCID 67461726 | HCID 67461726 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 71279055 | HCID 71279055 | — |
Reaction Steps
In a screw cap vessel Compound 306 (0.017 g, 0.06 mmol) and 3-bromomethyl-3-hydroxymethyl-oxetane (0.22 g, 0.12 mmol) were dissolved in DMF (0.5 mL) and K2CO3 (0.02 g, 0.15 mmol) was added. The suspension was heated at 100° C. for 3 h. H2O (3 mL) was added and the suspension was extracted with EtOAc (3×3 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. In a screw cap vessel the crude product was dissolved in CH3CN (0.2 mL). Triethyl amine (0.003 mL) and Ethyl isocyanate (0.044 mL, 0.6 mmol) were added. The mixture was heated at 50° C. for 18 h and the solvent was evaporated. The crude product was purified by flash chromatography using toluene:EOAc 60:40->40:60 as the eluent. This afforded the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051290B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-355e5e85196a4c75bacef0b614878d34 |
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| Source note | uspto-grants-2015_06 |
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