Carbon Tetrachloride → HCID 9862135, compound

Participants

Reaction Steps

(-)-5-Acetamidomethyl-3-(3-fluoro-4-(3-hydroximino-pyrrol-1-yl)phenyl)isoxazoline (Example 16) (486 mg) is combined with triphenylphosphine (1.48 g) and carbon tetrachloride (0.816 ml) in 14 ml acetonitrile in a 50 ml one neck round bottom flask under nitrogen. The mixture is stirred 1 hour at room temperature and the volatiles are removed in vacuo to give a pale yellow oil. The crude material is chromatographed over 35 g silica gel (230-400 mesh) eluting with 4% methanol/dichloromethane while collecting 5 ml fractions. Fractions 39-50 are combined and concentrated to give 224 mg of a white solid. The solid is washed with diethyl ether and is dried to give 160 mg of the title compound as a white solid, mp 159-161° C., [α]25D -72° (c 0.53, DMSO).

Provenance & Evidence