Sodium Bicarbonate → HCID 131721998, compound

Participants

Reaction Steps

Compound 18 (7.33 g, 8.99 mmol) was prepared from 16 (5.30 g, 9.99 mmol), 15 (4.13 g, 10.0 mmol), and NaHCO3 (2.52 g, 30.0 mmol) in 90% yield by the same method used for the preparation of 17. For 18: mp 138-140° C.; 1H NMR (DMSO-d6) d 1.50 (s, 9H, 3×CH3), 3.72, 3.83 (AB, Jgem =19 Hz, 2H, CH2S), 4.60 (s, 2H, OCH2CO), 4.99, 5.29 (AB, Jgem =15 Hz, 2H, CH2O), 5.18 (d, J=5.0 Hz, 1H, HC(6)), 5.79 (dd, J=5.0 and 9.5 Hz, 1H, HC(7)), 6.20 (br, 3H, 3×OH), 6.90-7.50 (m, 14H, 4×ArH), 8.30 (d, J=9.5 Hz, 1H, NH); IR (nujol): 3290-3370 (OH, NH), 1792 (β-lactam), 1750 (ester), 1730 (ester), 1688 (amide), 1620 (C=O) cm-1. Anal. (C41H35N2O12SCl) C, H, N, S, Cl.

Provenance & Evidence