Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 67814345 | HCID 67814345 | — |
| Reactant | HCID 178418918 | HCID 178418918 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 67815309 | HCID 67815309 | 80.7% |
Reaction Steps
To a round bottomed flask was added ethyl 2-(5-((S)-1-amino-2,2,2-trifluoroethyl)-3-methylisoxazol-4-yl)benzoate (124.2 mg, 0.378 mmol) and THF (2 mL) before the solution was cooled to −40° C. To this solution was added isopropylmagnesium chloride (473 μl, 0.946 mmol) and the reaction warmed to room temperature. The solution was diluted with NH4Cl solution and EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (86 mg, 0.305 mmol). LC/MS m/z 283 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796261B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-9783ba924db749dcaed382746bc386d5 |
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| Source note | uspto-grants-2014_08 |
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