Trisodium citrate → HCID 88208257, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of anisole (2.38 ml) and dichloromethane (1.2 ml) under argon was cooled to -20° C. and treated with aluminium chloride (61 mg). The mixture was stirred at -20° C. for 15 min. an then a slurry of 4-methoxybenzyl (6S, 7S)-7-[2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-8-oxo-3-(tetrahydrofuran-2-yl)-1-aza-4-oxabicyclo[4.2.0]oct-2-ene-2-carboxylate (I) (88 mg) in dichloromethane (7.5 ml) was added. The mixture was stirred for 5 min. and then trisodium citrate (5.2 ml of 0.5M) was added and the mixture stirred for 10 min. The aqueous phase was separated and washed twice with dichloromethane, then evaporated. The product was purified by HP20SS chromatography of the residue (water with increasing proportions of acetone as eluent). Fractions containing product were combined and evaporated and the residue dissolved in water (4 ml) and freeze-dried to give the title compound (27 mg). νmax (KBr) 1757, 1662 and 1617 cm-1 ; δ[(CD3)2SO]1.68-1.95 (4H, m), 3.58-3.77 (4H, m), 3.84 (3H, s), 4.35 (1H, m), 5.51 (1H, dd, J 3.91 and 8.83 Hz), 5.68 (1H, t, J 6.84), 6.78 (1H, s), 7.25 (2H, s), 9.91 (1H, d, J 8.83 Hz).

Provenance & Evidence