Dimethylformamide → HCID 178431941, compound

Participants

Reaction Steps

To a stirred solution of 644 mg. of 6-(2-[2-bromoacetamido]-2-phenylacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam in 15 ml. of N,N-dimethylformamide is added 45 mg. of 4-mercaptopyridine followed by 0.19 ml. of triethylamine. Stirring is continued for 3 hours at 25° C., and then the reaction solution is added dropwise into 200 ml. of vigorously stirred chloroform. The precipitate is removed by filtration, and the filtrate is added dropwise with stirring to 400 ml. of hexane. This causes the product to precipitate. After being slurried with methylene chloride, it weighs 228 mg. (33% yield), m.p. 182°-198° C. (dec.). IR (KBr disc): 1780 cm-1 (β-lactam) and 1667 cm-1 (amide I). NMR (DMSO-d6 /D2O): 8.33 ppm (d,4H), 7.33 (s,5H), 5.60 ppm (m,3H), 5.15 ppm (s,1H), 3.68 ppm (s,2H), 1.47 ppm (s,3H), 1.00 ppm (s,3H).

Provenance & Evidence