Potassium Carbonate → Cefuroxime Pivoxetil

反応式

[CH3:1][O:2]/[N:3]=[C:4](\[C:10]([NH:12][C@@H:13]1[C:16](=[O:17])[N:15]2[C:18]([C:27]([OH:29])=[O:28])=[C:19]([CH2:22][O:23][C:24]([NH2:26])=[O:25])[CH2:20][S:21][C@H:14]12)=[O:11])/[C:5]1[O:9][CH:8]=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:37]([O:39][C:40](=[O:46])[C:41]([O:44][CH3:45])([CH3:43])[CH3:42])[CH3:38]>CN(C)C=O>[C:24]([O:23][CH2:22][C:19]1[CH2:20][S:21][C@@H:14]2[C@H:13]([NH:12][C:10](=[O:11])/[C:4](=[N:3]\[O:2][CH3:1])/[C:5]3[O:9][CH:8]=[CH:7][CH:6]=3)[C:16](=[O:17])[N:15]2[C:18]=1[C:27]([O:29][CH:37]([O:39][C:40](=[O:46])[C:41]([O:44][CH3:45])([CH3:43])[CH3:42])[CH3:38])=[O:28])(=[O:25])[NH2:26]

参加物

実験手順

Cefuroxime (4.24 g) and powdered potassium carbonate (0.690 g) were stirred in anhydrous N,N-dimethylformamide (40 ml) till a solution was obtained. The solution was cooled to -3°, 2-methoxy-2-methylpropanoic acid 1-bromoethyl ester (2.50 g) was added and the solution was stirred for 1 hour. It was then partitioned between 2N hydrochloric acid (100 ml) and ethyl acetate (200 ml and 100 ml) and the combined organic layers were washed sequentially with 100 ml each of 2N hydrochloric acid (2×), water, saturated aqueous sodium bicarbonate, water (2×) and saturated brine, dried over magnesium sulphate and concentrated under reduced pressure to ca 20 ml. The solution was added slowly to petroleum ether (200 ml) and the resulting precipitate was filtered off, washed with petroleum ether and dried under vacuum to give the title ester (2.20 g); λmax (ethanol) 277.5 nm E11 342; νmax (CHBr3) 3520 and 3400 (NH and NH2), 1788 (β-lactam C=O), 1750 (ester C=O), 1732 (αβ unsaturated ester and carbamate C=O), and 1688 and 1514 cm-1 (amide C=O).