HCID 131721999, compound → HCID 70246610, compound

Participants

Reaction Steps

A solution of 17 (3.93 g, 4.99 mmol) in CF3CO2H (35%) in CH2Cl2 (45 mL) was stirred at room temperature for 13 h. The solution was condensed under reduced pressure and then CCL4 (30 mL) was added to the residue and evaporated. The resultant solid was crystallized from a mixture of EtOH and ether (2:1) to afford pure 19 (3.28 g, 4.49 mmol) as a white crystal in 90% yield: mp 196-198° C.; 1H NMR (DMSO-d6/D2O) d 3.60 (br s, 4 H, 2×CH2), 3.68, 3.79 (AB, Jgem=19 Hz, 2 H, CH2S), 4.65 (s, 2 H, OCH2CO), 4.95 5.25 (AB, Jgem=14 Hz, 2 H, CH2O), 5.15 (d, J=5.1 Hz, 1 H, HC(6)), 5.76 (d, J=5.1 Hz, 1 H, HC(7)), 6.80-7.35 (m, 14 H, 4×ArH); IR (nujol): 3300-3450 (OH, NH, CO2H), 1785 (β-lactam), 1720 (ester), 1685 (amide), 1610 (C═O) cm−1. Anal. (C37H31N2O10SCl) C, H, N, S, Cl.

Provenance & Evidence