Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Pivaloyl chloride | HCID 62493 | — |
| Reactant | Benzeneacetic acid, 4-bromo- | HCID 74654 | — |
| Reactant | (R)-4-Benzyl-2-oxazolidinone | HCID 2734969 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 54374212 | HCID 54374212 | 83% |
Reaction Steps
2-(4-Bromophenyl)acetic acid (7.85 g, 36.5 mmol) and (R)-4-benzyloxazolidin-2-one (3.23 g, 18.3 mmol) were combined in toluene (30 mL) and triethylamine (10.2 mL, 73.0 mmol). The solution was then heated to 80° C., and a solution of pivaloyl chloride (4.49 mL, 36.5 mmol) in toluene (7.5 mL) was added slowly. The reaction was heated to 110° C. and stirred overnight. The reaction was then cooled, and the toluene solution was washed with 2N HCl, water, 5% Na2CO3, brine and then dried over Na3SO4. After removal of the solvent, the residue was purified by column chromatography to give (R)-4-benzyl-3-(2-(4-bromophenyl)acetyl)oxazolidin-2-one (5.65 g, 83%) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08372842B2 |
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| Source dataset | uspto-grants-2013_02 |
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| ORD ID | ord-d3ade4ffde3849ab8e04cfb750c56c94 |
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| Source note | uspto-grants-2013_02 |
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