Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Pyrrolidone | HCID 12025 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl 2-bromo-4-(trifluoromethyl)-1,3-oxazole-5-carboxylate | HCID 53403202 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57461786 | HCID 57461786 | 34% |
Reaction Steps
NaH (0.060 mg, 1.5 mmol) (60%) was added to a solution of 2-oxopyrrolidine (0.13 g, 1.5 mmol) in DMF (5.0 mL) at −78° C. followed by stirring for 15 mins at −78° C. Then ethyl 2-bromo-4-trifluoromethyloxazole-5-carboxylate A-2 (0.29 g, 1.0 mmol) was added. The reaction mixture was stirred for 3 h while the temperature was slowly warmed to RT. The reaction mixture was purified by chromatography on a Prep Gilson HPLC to yield ethyl 2-(2-oxopyrrolidin-1-yl)-4-(trifluoromethyl)oxazole-5-carboxylate (A-30) as a white solid (0.15 g, 34% yield). 1H NMR (500 MHz, CDCl3) δ 4.44 (m, 2H), 4.09 (t, 2H, J=7.0 Hz), 2.69 (t, 2H, J=8.2 Hz), 2.28 (m, 2H), 2.42 (t, 3H, J=7.3 Hz).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08716312B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-3b5624521ff742b9b6d750afeec36938 |
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| Source note | uspto-grants-2014_05 |
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