Bromoacetic Acid → HCID 178431939, compound

Participants

Reaction Steps

To a stirred slurry of 4.27 g. (10 mmole) of 6-(2-amino-2-phenylacetamido)-2,2-dimethyl-3-(5-tetrazolyl)penam in 25 ml. of water, at 0° C., is added 1.39 g. (10 mmole) of bromoacetic acid in 6 ml. of water. The pH is adjusted to 6.0, and then 1.9 g. (10 mmole) of 1-ethyl-3-(dimethylaminopropyl)-carbodimide hydrochloride in 9 ml. of water is added. The mixture is stirred for 3 hours at pH 6. At this point, the pH is raised to 7.0, and the reaction mixture is washed with ethyl acetate. The pH is then lowered to 2.0, and the product is extracted into ethyl acetate. The dried extracts are concentrated to dryness in vacuo to give 2.0 g. (40% yield) of the title compound, m.p. 128°-135° C. IR (KBr disc): 1800 cm-1 (β-lactam) and 1653 cm-1 (amide I). NMR (in DMSO-d6 /D2O): 7.43 ppm (s, 5H), 5.73 ppm (s, 1H), 5.63 ppm (m, 2H), 5.23 ppm (s, 1H), 4.02 ppm (s, 2H), 1.60 ppm (s, 3H), 1.00 ppm (s, 3H).

Provenance & Evidence