Hydrochloric Acid → 7-Amino-3-(4-carboxypyridin-2-yl)thiomethyl-3-cephem-4-carboxylic acid
Reaction equation
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.[S-:19][C:20]1[CH:25]=[C:24]([C:26]([O-:28])=[O:27])[CH:23]=[CH:22][N:21]=1.[Na+].[Na+].C(=O)(O)[O-].[Na+].Cl>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:19][C:20]3[CH:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][N:21]=3)[CH2:15][S:14][C@H:9]12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a suspension of 7-aminocephalosporanic acid (9.30 g) and disodium 2-sulfido-4-pyridinecarboxylate (6.80 g) in water (160 ml) was dropwise added sodium bicarbonate (5.73 g) at room temperature. To the resulting mixture was added a saturated aqueous solution of sodium bicarbonate so that the pH was adjusted to 6.8. The resulting mixture was warmed to 65° C. and stirred for 1.5 hours during which period the temperature was allowed to rise from 65° to 75° C. The reaction mixture was cooled and then adjusted to pH 3.6 with 10% hydrochloric acid. The precipitates were collected by filtration, washed successively with water (×2), acetone (×2) and diethyl ether and then dried to give 7-amino-3-(4-carboxypyridin-2-yl)thiomethyl-3-cephem-4-carboxylic acid (6.61 g).
Workup
- customat room temperature
- customto rise from 65° to 75° C
- temperatureThe reaction mixture was cooled
- filtrationThe precipitates were collected by filtration
- washwashed successively with water (×2), acetone (×2) and diethyl ether
- customdried
Sources & evidence
- ORD record
- ord-d34dde924166459d85cab9d109db050d
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04529802
Reaction notes
Loading…