[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6]([NH2:9])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.[CH3:20][C:21](=[CH2:23])[CH3:22]>COCCOC>[NH2:9][C@@H:6]1[C:7](=[O:8])[N:4]2[C:3]([C:12]([O:14][C:21]([CH3:23])([CH3:22])[CH3:20])=[O:13])=[C:2]([CH3:1])[CH2:11][S:10][C@H:5]12A mixture of 7-ADCA (10.0 g, 0.0467 mol), ethylene glycol dimethyl ether (80 ml), concentrated sulfuric acid (6.0 ml) and isobutylene (36.0 g, 0.6416 mol) in a pressure bottle was stirred at room temperature for 32 hours. Solvent was removed under reduced pressure. The residue was diluted with methylene chloride, washed with water, sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated to give 4.18 g of t-butyl 7β-amino-3-methyl-3-cephem-4-carboxylate.
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