Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethylphosphite | HCID 3780918 | — |
| Reactant | HCID 10175195 | HCID 10175195 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 10128237 | HCID 10128237 | 44% |
Reaction Steps
(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(2,2-dibromoethenyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (0.4 g, 0.69 mmol) was dissolved/supended in ethanol (2 ml) and diethylphosphite (0.36 ml, 2.79 mmol). Triethylamine (0.195 ml, 1.39 mmol) was added and the reaction mixture heated under vigorous stirring at 90° C. for 5 hours. It was cooled to room temperature, diluted with dichloromethane, washed with phosphate buffer (pH 7) and dried over sodium sulfate. Chromatography on silica gel with dichloromethane/DMF (50:1 to 40:1) gave 151 mg (44%) of the title compound as a colourless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07199143B2 |
|---|
| Source dataset | uspto-grants-2007_04 |
|---|
| ORD ID | ord-edb379f727794d8fa54c9f0258c4d3e1 |
|---|
| Source note | uspto-grants-2007_04 |
|---|