2,6-Lutidine → HCID 54167408, compound

Participants

Reaction Steps

To a solution of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-formamidoacetate (2.70 g.) and 2,6-lutidine (11.4 ml.) in methylene chloride (16 ml.) was added dropwise phosphorus oxychloride (1.12 ml.) at 0° C. After stirring at the same temperature for 4.8 hours, the mixture was diluted with a mixture of benzene and ethyl acetate (120 ml.) (6:4 by volume), and washed successively with a chilled dilute aqueous solution of sodium chloride, a mixture of 10% phosphoric acid (75 ml.) and a saturated aqueous solution of sodium chloride, a dilute aqueous solution of sodium chloride, ice-water and a saturated aqueous solution of sodium chloride. Drying over magnesium sulfate and removal of the solvent left an oil (2.5 g.), which was chromatographed on silica gel (30 g.) with a mixed solvent of benzene and ethyl acetate (5:1 by volume) as an eluent to give an amorphous solid of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1 -azetidinyl]-2-isocyanoacetate.

Provenance & Evidence