Pyridine → HCID 131715962, compound

Participants

Reaction Conditions

Reaction Steps

7-Amino-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid pivaloyloxymethyl ester (0.229 g) as prepared in Reference Example 1 above was dissolved in methylene chloride (5 ml). The resultant solution was admixed with 2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid (syn-isomer) (0.235 g) and methylene chloride (5 ml). To the mixture obtained were further added pyridine (0.07 ml) and then dropwise phosphorus oxychloride (0.07 ml) at -20° C. The reaction mixture was stirred for 10 minutes at 0° C. and poured into a mixture of ice-water (50 ml) and ethyl acetate (50 ml). After stirring, the organic phase was separated from the aqueous phase and washed with ice-wated and then with ice-cooled aqueous saturated sodium hydrogen carbonate solution. The organic phase was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified chromatographically on a column of silica gel (Wako gel C-300) (20 g ) as developed with benzene-ethyl acetate (5:1) as the development solvent. 7-[2-Methoxyimino-2(2-tritylaminothiazol-4yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid (syn-isomer) pivaloyloxymethyl ester (0.184 g) was obtained.

Provenance & Evidence