反应详情

Triphenylphosphine (2.82 g, 10.8 mmol) was added portionwise to a solution of 5-(S)-azidomethyl-3-[4′-triphenylmethylthio-3′-fluorophenyl]-oxazolidine-2-one (5.00 g, 9.79 mmol) in THF (40 mL), and the mixture stirred for 2 h at room temperature. Water (1.41 mL, 78.3 mmol) was added, and the mixture heated at 40° C. overnight. Solvent was removed under vacuum, and the oily residue dissolved in dichloromethane (50 mL). Acetic anhydride (4.62 ml, 49.0 mmol) and pyridine (7.92 ml, 97.9 mmol) were added, and the mixture stirred for 8 h at r.t. Solvent was removed under vacuum and the crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes) to give the product as a foam (4.98 g, 97%); MS: 527 [M+H]+. 1H NMR.

1. temperaturethe mixture heated at 40° C. overnight
2. customSolvent was removed under vacuum
3. dissolutionthe oily residue dissolved in dichloromethane (50 mL)
4. stirringthe mixture stirred for 8 h at r.t
5. customSolvent was removed under vacuum
6. customthe crude product purified by silica gel flash column chromatography (eluent: 30% ethyl acetate in hexanes)