Phosphoric Acid → HCID 88840158、化合物

反応式

CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[C:19](=[O:22])(O)[O-].[Na+].P([O-])([O-])([O-])=O.[CH3:29][C:30]1[N:31]=[CH:32][S:33][C:34]=1[CH3:35].[S:36]1C=CC=C1C(O)=O.P(=O)(O)(O)O>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:36][C:19]([C:32]3[S:33][C:34]([CH3:35])=[C:30]([CH3:29])[N:31]=3)=[O:22])[CH2:15][S:14][C@H:9]12

参加物

反応物 5

HCID 1004Phosphoric Acid

HCID 1061Phosphate

HCID 4413287-Aminocephalosporanic acid

HCID 516892Sodium Bicarbonate

HCID 86734074HCID 86734074、化合物

生成物 1

HCID 88840158HCID 88840158、化合物収率 45%

実験手順

To a stirred solution of 7.22 g. (0.0265 mole) of 7-aminocephalosporanic acid and 4.45 g. (0.053 mole) of sodium bicarbonate in 160 ml. of aqueous phosphate buffer (ph 6.4) was added 4.6 g. (0.0265 mole) of 4,5-dimethylthiazole-2-thiolcarboxyic acid. The mixture was stirred in a nitrogen atmosphere and heated to 50°. The pH was adjusted from 7.0 to 6.5 with 42% phosphoric acid. A crystalline solid started to precipitate. After 5 hours at 50° the reaction mixture was cooled to 20°. The precipitated solid was collected by filtration, washed with water and acetone and dried in vacuo over phosphorus pentoxide to provide 4.55 g. of a tan crystalline material. Yield = 45%. NMR spectrum was consistent with structure.