Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | (5R)-3-[4-(3,6-Dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[(4-ethoxy-1H-1,2,3-triazol-1-yl)methyl]-2-oxazolidinone | HCID 10127293 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 10173091 | HCID 10173091 | 60.8% |
Reaction Steps
(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-ethoxy-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 35) (390 mg, 0.89 mmol) was dissolved in dry dichloromethane (5 ml), cooled down to 0° C., boron tribromide was added via syringe, then the mixture was warmed up to 45° C. and stirred for 48 hours. It was quenched dropwise with water (10 ml) and was extracted with dichloromethane. The combined organic layer was concentrated under vacuum and the residue was purified by reverse phase chromatography with 5%–95% acetonitrile in water (containing 0.1% TFA) to give the title product (221 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07199143B2 |
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| Source dataset | uspto-grants-2007_04 |
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| ORD ID | ord-0e86c7e8d7d246dea50c0a264535caaa |
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| Source note | uspto-grants-2007_04 |
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