Hydrochloric Acid → Imipenem

Participants

Reaction Steps

Thienamycin (517 mg) is dissolved in pH 7 0.1 N phosphate buffer (25 ml) and cooled in an ice bath with magnetic stirring. The solution is adjusted to pH 8.5 using 2.5 N sodium hydroxide solution dispensed from an automatic burette. While maintaining a pH of 8.5, methyl formimidate hydrochloride (711 mg) is added portionwise over a 2-3 minutes. After an additional 10 minutes, the pH of the solution is brought to 7.0 using 2.5 N hydrochloric acid. The solution is chromatographed on a column of XAD-2 resin (150 cc) which is eluted with water. The N-formimidoyl Thienamycin derivative elutes in 1.5-2.0 column volumes (200-300 cc) and is lyophilized to a white solid (217 mg). UV (pH 7 0.1 N phosphate buffer)λmax 297 nm (8,590). ir (Nujol mull) 1767 cm-1 (β-lactam) nmr (D2O)δ1.37 (d, J=6 Hz, CH3 --CH), 3.0-3.75 (m, --CH2 --), 4.2-4.8 (m, C5H, C6H, C7H), 7.86 ##STR76##

Provenance & Evidence