Hydrochloric Acid → 2-Methyl-7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid
Reaction equation
Cl.[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[N:6]2[C:12](=[O:27])[CH:13]([NH:14][C:15](=[O:26])[C:16](=[N:23][O:24][CH3:25])[C:17]3[N:18]=[C:19]([NH2:22])[S:20][CH:21]=3)[C@H:5]2[S:4]1.C(=O)(O)[O-].[Na+].Cl>O>[CH3:2][CH:3]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[N:6]2[C:12](=[O:27])[CH:13]([NH:14][C:15](=[O:26])[C:16](=[N:23][O:24][CH3:25])[C:17]3[N:18]=[C:19]([NH2:22])[S:20][CH:21]=3)[C@H:5]2[S:4]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 2-methyl-7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid hydrochloride (syn isomer), which can be represented as 2-methyl-7-[2-methoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid hydrochloride (syn isomer), (7.7 g.) in water (77 ml.) was added a saturated aqueous sodium bicarbonate solution (44 ml.). Thus obtained solution was adjusted to pH 3 with 1 N hydrochloric acid and then allowed to stand for 1 hour at cold place. The precipitated crystals were collected by filtration, washed with water and then dried to give white powder of 2-methyl-7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer), which can be represented as 2-methyl-7-[2-methoxyimino-2-(2-imino-2,3-dihydrothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (6.67 g.), mp 196° to 240° C. (dec.).
Workup
- filtrationThe precipitated crystals were collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-e18bbb0d038b4c16be70c2bb14767c36
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04225707
Reaction notes
Loading…