C(=O)(O)[O-].[Na+].CC(O[CH2:10][C:11]1[CH2:20][S:19][C@@H:14]2[C@H:15]([NH2:18])[C:16](=[O:17])[N:13]2[C:12]=1[C:21]([OH:23])=[O:22])=O.[Na].[NH2:25][N:26]1[C:30]([SH:31])=[N:29][N:28]=[N:27]1.CS(O)(=O)=O>O>[NH2:18][C@@H:15]1[C:16](=[O:17])[N:13]2[C:12]([C:21]([OH:23])=[O:22])=[C:11]([CH2:10][S:31][C:30]3[N:26]([NH2:25])[N:27]=[N:28][N:29]=3)[CH2:20][S:19][C@H:14]12To a solution of sodium bicarbonate (9.24 g, 0.11 mol) in water (1 liter) was added 7β-aminocephalosporanic acid (27.2 g, 0.1 mol) and the mixture was stirred until solution results. The sodium salt of 1-amino-5-mercapto-1H-tetrazole (27.8 g, 0.2 mol) was added to the mixture and allowed to react in an argon stream between 52° C. and 53° C. for 3 hours. An additional amount of the sodium salt of 1-amino-5-mercapto-1H-tetrazole (6.95 g, 0.5 mol) was added to the mixture and allowed to react at the same temperature for 2 hours. The mixture was then passed three times through a layer of activated carbon (15 g) in order to decolorize it. The filtrate was adjusted to pH 4.6 with methanesulfonic acid (about 6 ml) under ice-cooling and set aside to precipitate. The precipitated substance was filtered, washed with water and dried in vacuo over phosphorus pentoxide to give ocherous powder of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (17.3 g, 52%), mp~206° C. (decomposition).
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