HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → HCID 178448141, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | N-{(S)-2-hydroxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide | HCID 66645749 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178448141 | HCID 178448141 | 74% |
Reaction Steps
2.95 ml of a solution of diethyl azodicarboxylate in toluene (40%) (6.48 mmol) was added to a solution of 2.01 g of N-{(S)-2-hydroxy-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide obtained in Example (116f) (5.4 mmol) and 1.7 g of triphenylphosphine (6.48 mmol) in tetrahydrofuran (54 ml) under ice-cooling over five minutes, and the mixture was stirred at the same temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: toluene/acetone=5/1) to obtain 1.4 g of the title compound (yield: 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08158790B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-c97e2292836f467faa839cdab7327411 |
| Source note | uspto-grants-2012_04 |