Acetic Anhydride → HCID 12905414, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl 6-(α-Hydroxyethyl)-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (I) (18 mg) is dissolved in 1 ml of pyridine (Py) and 0.2 ml of acetic anhydride (Ac2O). The mixture is stirred at 25° C. for 3 hours and then evaporated to dryness to give oily residue. The residue is dissolved in 0.2 ml chloroform and chromatographed on two 20×20 cm, 250μ silica gel TLC plates (Rf 0.56, 20% ethylacetate/chloroform) to give 4 mg. of the desired product (II) which shows nmr (CDCl3, 60 MHZ) resonances at 2.02 (s, OAc), 6.48 (t, vinyl proton) and 7.40 ppm (m, aromatic protons) and ir (CHCl3) carbonyl vibrations at 1780 (β-lactam) and 1740 cm-1 (esters).

Provenance & Evidence