Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclobutanecarbonyl chloride | HCID 78705 | — |
| Reactant | HCID 15451838 | HCID 15451838 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 178429850 | HCID 178429850 | — |
Reaction Steps
The imine (Example 26A, 30 mg, 0.09 mmol) was dissolved in 1.5 ml acetonitrile (1.5 mL). Triethylamine (19 μl, 0.18 mmol) was added followed by the cyclobutanecarbonyl chloride (0.11 mmol). The reaction was heated at 65° C. overnight. The reaction mixture was cooled down and passed through a Si-amine cartridge (1 g, 1.6 mmol/g) to remove the excess carbonyl chloride eluting with additional acetonitrile. The resulting solution was dried and purified by reverse phase HPLC. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.75 (1H), 1.88 (1H), 2.10 (4H), 2.26 (3H), 3.15 (1H), 7.44 (1H), 7.63 (1H), 7.68 (1H), 7.90 (1H); MS (ESI) m/z 403.0 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07683084B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-064dc825fc0c4e388367788e76fc54b7 |
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| Source note | uspto-grants-2010_03 |
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