Potassium Bromide → Clavulanic Acid

Participants

Reaction Steps

Benzyl clavulanate (840 mgs) in ethanol (30 ml) and water (5 ml) was hydrogenated over 10% Pd/C (267 mgs) and sodium bicarbonate (244 mgs) for 25 minutes at room temperature and atmospheric pressure. The catalyst was filtered, washed with water and ethanol and the combined filtrates were evaporated in vacuo. The product crystallised from a water-acetone mixture as microneedles (565 mgs). Recrystallisation from water-acetone gave needles which, after drying over P2O5 in vacuo for 24 hours gave the following analysis: C 41.01, 40.86; H 3.77, 3.64; N 5.68, 5.51; i.r.(KBr disc) 1785, 1700, 1620 cm−1; Nmr (D2O) 3.06 (d,1,J=18.5 Hz), 3.57 (dd,1,J1=18.5 Hz, J2=2.5 Hz), 4.15 (d,2,J=8 Hz), 5.3 (HOD), 4.9 (m), 5.71 (d,1,J=2.5 Hz).

Provenance & Evidence