Potassium Carbonate → HCID 54474289, compound

Participants

Reaction Steps

(RS)-2-Chloroacetyltetrahydrothiophene (2.50 g), (3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-one (4.60 g) and potassium carbonate (2.52 g) in DMF (30 ml) were stirred at room temperature for 2.5 h. T.l.c. analysis (ethyl acetate) showed completion of the reaction. The reaction mixture was diluted with ethyl acetate, washed with water (3×), brine and then dried. The solvent was evaporated and the residue flash chromatographed on silica gel eluting with 80% ethyl acetate/hexane to give the title compound as a pale yellow solid (4.194 g, 73%); m.p. 123° C., ethyl acetate/hexane; (Found: C, 53.51; H, 5.00; N, 7.39; S, 17.06%. C17H20N2O4S2 requires C, 53.66; H, 5.30; N, 7.36; S, 16.85%); νmax (CH2Cl2) 3405, 1785 and 1695 cm-1 ; δH (CDCl3), 1.81-1.95 (1H, m), 2.01-2.12 (2H, m), 2.28-2.42 (1H, m), 2.88 (2H, t, J 6.5 Hz), 3.39 and 3.56 with 3.39 and 3.45 (2H, 2 ABq, J 5.9 Hz), 4.07 and 4.09 (1H, 2 t, J 3.8 and 3.7 Hz), 4.58 (2H, s), 5.00 and 5.04 (1H, 2d, J 4.6 Hz), 5.58 and 5.60 (1H, 2 dd's,J 4.6, 9.2 Hz), 6.55 and 6.64 (1H, 2 br s), 6.94-7.07 (3H, m), 7.27-7.36 (2H, m), and 7.46 and 7.47 (1H, 2 br d, J 9.2 Hz).

Provenance & Evidence