Triphenylphosphine → 5(r)-1,2,5-Thiadiazol-3-yloxymethyl-3-phenyloxazolidin-2-one

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Reaction Steps

Diisopropylazodicarboxylate (4.45 g, 22 mmol) was added dropwise to a stirred solution of 5(R)-hydroxymethyl-3-phenyloxazolidin-2-one (Gregory et al. J. Med, Chem, 32, 1673 (1989); 4.25 g,22 mmol), triphenyl phosphine (5.76 g, 22 mmol) and 3-hydroxy-1,2,5-thiadiazole (Weinstock et al, J.Org. Chem, 32, 2823 (1967)) (2.04 g, 20 mmol) in 30 ml THF, in an ice-bath. After stirring at ambient temperature for two hours and evaporating in vacuo, the resulting oil was purified by chromatography (Merck 9385 silica. Gradient elution from isohexane to ca. 50% EtOAc/isohexane to give a white solid. Further purification by flash chromatography on silica using 1% MeOH/dichloromethane was necessary to remove remaining diisopropylcarboxyhydrazine yielding the title product as a white crystalline solid (4.7 g, 83%). MS: ESP+ (M+H)+=278.

Provenance & Evidence