Methanol → HCID 20550991, compound

Participants

Reaction Conditions

Reaction Steps

7-Amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1 g, 4.67 mmol) was suspended in methanol (20 mL) before treating with conc. sulphuric acid (0.1 ml, 1.876 mmol) and heated at reflux (75° C.) for 16 hours, under argon. After heating for 15 minutes all the remaining solid had dissolved to form a yellow solution. The solution turned from yellow to brown overnight. LCMS run. Desired product seen. Reaction cooled to RT, amount of solvent reduced in vacuo. Residue partitioned between EtOAc (40 ml) and saturated sodium bicarbonate solution (40 ml). Layers separated and aqueous layer was extracted with EtOAc (2×30 ml). Combined extracts were washed with brine (30 ml), dried over Na2SO4, filtered and evaporated to afford a brown gum of the desired product in 801 mg.

Provenance & Evidence